Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (2024)

2025 Day-to-Day

Expand All | Collapse All

Where to Arrive

Airport:

Portland International Airport (PDX)

Pick-up location:

Portland Marriott Waterfront, Portland, Oregon

Pick-up time:

9:00 AM

Where to Depart

Airport:

Portland International Jetport (PWM)

Drop-off location:

Press Hotel, Portland, Maine

Drop-off time:

11:00 AM

Additional Arrival Information

We suggest that you arrive at least one day prior to the start of your bike across America adventure, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays.

We recommend that you fly into Portland International Airport (PDX), which is approximately 12 miles from downtown Portland. You can hail a taxi outside baggage claim, which will cost approximately $35 plus gratuity and should take about 30 minutes, depending on traffic.

Your Trek Travel guides will meet you at the Portland Marriott Downtown Waterfront (1401 SW Naito Pkwy, Portland, OR) at 9:00 AM on the first day of the trip. You will then shuttle approximately two hours to Astoria for a picnic and bike fit followed by your first ride. Please feel free to dress comfortably for the shuttle, but keep your riding clothes and gear handy and separate from your main luggage. You will be able to change at the hotel before the ride. Your main luggage will be stored until your room is ready.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. If you cannot reach them, please call our first hotel, Cannery Pier Hotel (503-325-4996), and leave a message with your expected arrival time and contact details.

Additional Departure Information

You will say farewell to your guides at 11:00 AM at the Press Hotel. We recommend that you fly out of the Portland International Jetport (PWM), which is located about six miles from downtown. A taxi can be arranged with assistance from the front desk, takes about 20 minutes and will cost approximately $25 plus gratuity.

Aug 21 - Astoria to Pacific Ocean

Overview

Your Trek Travel guides will meet you at the Marriott Downtown Waterfront Hotel at 9:00 AM on the first day of the trip. Today is the day to get everything in order before embarking on your cross-country odyssey. After a two-hour shuttle to the town of Astoria, you will enjoy a hearty welcome lunch and brief introductions, and your guides will take time to ensure you have a comfortable fit on your bike. We recommend that you have a professional bike fit early in you... Your Trek Travel guides will meet you at the Marriott Downtown Waterfront Hotel at 9:00 AM on the first day of the trip. Today is the day to get everything in order before embarking on your cross-country odyssey. After a two-hour shuttle to the town of Astoria, you will enjoy a hearty welcome lunch and brief introductions, and your guides will take time to ensure you have a comfortable fit on your bike. We recommend that you have a professional bike fit early in your training for the greatest efficiency and to reduce the risk of injury. Please bring your measurements, as well as your saddle, pedals, personal GPS unit, and any other equipment you would like affixed to your bike to this meeting so your guides can set up your bike to your requirements. Following the bike fit, safety tips and some introductory information, it's time for a short scenic spin from Astoria to Fort Stevens State Park and down to the Pacific Ocean where you can dip your wheel into the water to mark the official start of your journey. Use the rest of this ride to warm up your legs and make sure you are comfortable in the saddle. Your warm-up ride will be followed by a social hour and dinner, where your guides will discuss your upcoming adventure in more detail and answer any questions you may have. Read More

Hotel

Cannery Pier Hotel

Meals included

Lunch | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (1)

Highlight of the Day

Dip your wheel in the Pacific Ocean

Pedal to Shipwreck Point to commemorate the official start of this epic journey.

Ride Options

Ride Option 1

TODAY'S RIDE:

Astoria to Fort Stevens Return - Approximately 30 mi | 48 km and 789 ft | 240 m

Aug 22 - Astoria to Portland

Overview

Your adventure begins today as you depart Astoria and head for Portland on your first long ride of the trip! It's time to bid farewell to the West Coast and turn east as you ease into your first pedal strokes along Youngs River and through the beautiful and densely forested Clatsop State Forest. As you ride, the enclosed green canopy and winding roads gradually open up to bring you just north of Portland where you will continue southeast on the Scappoose-Vernonia Hi... Your adventure begins today as you depart Astoria and head for Portland on your first long ride of the trip! It's time to bid farewell to the West Coast and turn east as you ease into your first pedal strokes along Youngs River and through the beautiful and densely forested Clatsop State Forest. As you ride, the enclosed green canopy and winding roads gradually open up to bring you just north of Portland where you will continue southeast on the Scappoose-Vernonia Highway and directly into downtown. Explore one of America's most bike-friendly cities this evening as you relish the feeling of accomplishment from completing your first full day in the saddle. Read More

Hotel

Portland Marriott Downtown Waterfront

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (2)

Highlight of the Day

Ride through Portland

Get a glimpse of what makes Portland a Platinum level Bicycle Friendly Community during your first big ride.

Ride Options

Ride Option 1

TODAY'S RIDE:

Astoria, OR to Portland, OR - Approximately 100 mi | 161 km and 4,768 ft | 1,453 m

Aug 23 - Portland to Hood River

Overview

You'll depart Portland this morning on a network of popular bike trails and lanes. Once in Troutdale, you will ride on the Historic Columbia River Gorge Highway 30 that separates Washington from Oregon. The north side of this 75-mile scenic byway boasts spectacular views of the Columbia River Gorge while the south is blessed with a collection of astonishing waterfalls. Take the time to stop at Columbia Point, one of the most scenic outlooks on the journey, and visit... You'll depart Portland this morning on a network of popular bike trails and lanes. Once in Troutdale, you will ride on the Historic Columbia River Gorge Highway 30 that separates Washington from Oregon. The north side of this 75-mile scenic byway boasts spectacular views of the Columbia River Gorge while the south is blessed with a collection of astonishing waterfalls. Take the time to stop at Columbia Point, one of the most scenic outlooks on the journey, and visit the Vista House which was built as a rest stop for early travelers. As you finish your ride, don't forget to look out onto the river, as Hood River is renowned as one of the best windsurfing locations in the U.S. Tonight is yours to explore. Take a stroll down Oak Street and dine in one of the many tasty bistros. Read More

Hotel

Hampton Inn

Meals included

Breakfast | Lunch

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (3)

Highlight of the Day

Ride the Historic Columbia River Gorge Highway

Enjoy the view as you pedal along this scenic byway, including the famed Multnomah Falls.

Ride Options

Ride Option 1

TODAY'S RIDE:

Portland, OR to Hood River, OR - Approximately 75 mi | and 121 km and 3,750 ft | 1,143 m

Aug 24 - Hood River to Condon

Overview

Depart this windsurfing and mountain-biking hotspot to continue following the Lewis and Clark Trail along the water. Cycle through the five-mile Mosier Twin Tunnels Trail that passes through two climate zones and is bordered by numerous types of foliage and plants. The route hugs the Columbia River on Interstate 84 for about 15 miles before turning inland. Finish the day’s ride winding past rolling ranch lands, and tackling the climbs through Cottonwood Canyon Sta... Depart this windsurfing and mountain-biking hotspot to continue following the Lewis and Clark Trail along the water. Cycle through the five-mile Mosier Twin Tunnels Trail that passes through two climate zones and is bordered by numerous types of foliage and plants. The route hugs the Columbia River on Interstate 84 for about 15 miles before turning inland. Finish the day’s ride winding past rolling ranch lands, and tackling the climbs through Cottonwood Canyon State Park and Recreation Area. We’ll be spending the night in Condon, a proud, century-old farming community nestled between miles of rolling, golden wheat fields in Eastern Oregon. Read More

Hotel

Hotel Condon | Condon Motel

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (4)

Highlight of the Day

Stay at Historic Hotel Condon

Built in 1920, the historic Hotel Condon offers classic charm with a quaint, “small-town America” atmosphere.

Ride Options

Ride Option 1

TODAY'S RIDE:

Hood River, OR to Condon, OR - Approximately 94 mi | 151 km and 7,835 ft | 2,388 m

Aug 25 - Condon to Hermiston

Overview

After a hilly start this morning, we'll reach the small town of Heppner, known as the “Gateway to the Blues.” Pedal a short stretch of the Blue Mountain Scenic Byway before gradually descending back towards the Columbia River. Enjoy dinner at Nookie’s restaurant, home of the Hermiston Brewing Company & Tap House. This historic building housed a Plymouth dealership for many years in the early 1940s, but now offers over 15 beers produced in-house! Spend the nigh... After a hilly start this morning, we'll reach the small town of Heppner, known as the “Gateway to the Blues.” Pedal a short stretch of the Blue Mountain Scenic Byway before gradually descending back towards the Columbia River. Enjoy dinner at Nookie’s restaurant, home of the Hermiston Brewing Company & Tap House. This historic building housed a Plymouth dealership for many years in the early 1940s, but now offers over 15 beers produced in-house! Spend the night in Hermiston, once known as home of Six Mile House, an old-west hotel that served as a stopover for weary travelers, and is now famous for watermelon farms. Read More

Hotel

Holiday Inn Express

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (5)

Highlight of the Day

Cross the Blue Mountains

Continue to roughly follow the route of Lewis and Clark as you cross over the Blue Mountains.

Ride Options

Ride Option 1

TODAY'S RIDE:

Condon, OR to Hermiston, OR - Approximately 90 mi | 145 km and 4,087 ft | 1,246 m

Aug 26 - Hermiston to Walla Walla

Overview

Today is a relatively short ride as we make our way into Washington. Pedal through high-desert sage and the farmland producing the sweet onions, wheat, and wine that give Walla Walla its flavor. Finish your ride in the heart of town where the tree-lined streets are lined with a mix of vintage shops, boutiques, cafes, and bookstores. This evening, venture out to enjoy a wine tasting and dinner of your choice.

Hotel

Marcus Whitman or The Finch Hotel

Meals included

Breakfast | Lunch

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (6)

Highlight of the Day

Enter State #2 and discover Walla Walla

Walla Walla is one of the most beautiful towns in Washington and has over 30 tasting rooms featuring varietals from the surrounding wine cou... Walla Walla is one of the most beautiful towns in Washington and has over 30 tasting rooms featuring varietals from the surrounding wine country. Read More

Ride Options

Ride Option 1

TODAY'S RIDE:

Hermiston, OR to Walla Walla, WA - Approximately 70 mi | 113 km and 3,014ft | 919 m

Aug 27 - Walla Walla to Lewiston

Overview

Climb out of Walla Walla on gently rolling hills as you make your way through eastern Washington's beautiful golden fields of wheat. Today you will work hard to get to Idaho, the third state of your journey, but the effort will be well worth it as you enjoy a long, winding descent into the state alongside the gentle Asotin Creek and the powerful Snake River. Shortly after crossing the border you will find yourself in Lewiston, located at the confluence of the Snake ... Climb out of Walla Walla on gently rolling hills as you make your way through eastern Washington's beautiful golden fields of wheat. Today you will work hard to get to Idaho, the third state of your journey, but the effort will be well worth it as you enjoy a long, winding descent into the state alongside the gentle Asotin Creek and the powerful Snake River. Shortly after crossing the border you will find yourself in Lewiston, located at the confluence of the Snake and Clearwater Rivers. Due to a system of locks and dams, Lewiston is accessible by some ocean-going vessels and is the easternmost port on the west coast. Read More

Hotel

Hampton Inn

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Walla Walla, WA to Lewiston, ID - Approximately 98 mi | 158 km and 4,870 ft | 1,484 m

Aug 28 - Lewiston to Kamiah

Overview

Soon after departing Lewiston you will enter the land of the Nez Perce Native American tribe. Cruise through undulating hills and scattered towns as you uncover this magnificent gateway to the West. With many areas to hunt, fish, hike, and farm, the Nez Perce have made this area home since before the history of the West was recorded. Enjoy the striking views from the banks of the Clearwater River into the hills above as you make your way to the small town of Kamiah.

Hotel

Clearwater 12 Motel

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Lewiston, ID to Kamiah, ID - Approximately 80 mi | 129 km and 5,725 ft | 1,744 m

Aug 29 - Kamiah to Lolo

Overview

Today's epic ride follows the historic Route 12 into the Bitterroot Mountains and over Lolo Pass. You'll pedal along the banks of the Clearwater River this morning and the Lochsa River this afternoon, both of which are lined by majestic pines. Enjoy the serene yet striking scenery as you roughly follow in the footsteps of Lewis and Clark. The road climbs gently until the last few miles, which greet you with steeper terrain and sweeping views. Near the end of the rid... Today's epic ride follows the historic Route 12 into the Bitterroot Mountains and over Lolo Pass. You'll pedal along the banks of the Clearwater River this morning and the Lochsa River this afternoon, both of which are lined by majestic pines. Enjoy the serene yet striking scenery as you roughly follow in the footsteps of Lewis and Clark. The road climbs gently until the last few miles, which greet you with steeper terrain and sweeping views. Near the end of the ride, you'll reach the top of Lolo Pass at 5,233 feet, which is also the Montana border. Say hello to state number four and a new time zone! All that's left is a short descent to the Lodge at Lolo Hot Springs. It's a great place to rest and soak your legs after the day's climb. Read More

Hotel

The Lodge at Lolo Hot Springs

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (7)

Highlight of the Day

Enter State #4 and summit Lolo Pass

Enjoy breathtaking views as you climb along the Clearwater River and into the Bitterroot Mountains and Montana.

Ride Options

Ride Option 1

TODAY'S RIDE:

Kamiah, ID to Lolo, MT - Approximately 115 mi | 185 km and 6,451 ft | 1,966 m

Aug 30 - Lolo to Missoula

Overview

Enjoy a relaxed morning with your fellow riders as you get used to the time change, because this short day is nearly all downhill! Today you finish descending the gorgeous, winding road from Lolo Pass into the town of Missoula—home of the University of Montana. Take a look around at the peaks dominating the horizon, as this town lies at the convergence of five separate mountain ranges. It's your choice for lunch so enjoy your favorite foods as you soak in the scen... Enjoy a relaxed morning with your fellow riders as you get used to the time change, because this short day is nearly all downhill! Today you finish descending the gorgeous, winding road from Lolo Pass into the town of Missoula—home of the University of Montana. Take a look around at the peaks dominating the horizon, as this town lies at the convergence of five separate mountain ranges. It's your choice for lunch so enjoy your favorite foods as you soak in the scene in this fun college town. Tonight you will gather for a social hour and dinner at the hotel, as you raise a glass to congratulate each other on reaching your first well-earned rest day. Read More

Hotel

DoubleTree Hotel Missoula - Edgewater

Meals included

Breakfast | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (8)

Highlight of the Day

Enjoy a relaxing afternoon in Missoula

Celebrate the milestone of making it to your first rest day location.

Ride Options

Ride Option 1

TODAY'S RIDE:

Lolo, MT to Missoula, MT - Approximately 37 mi | 60 km and 587 ft | 178 m

Aug 31 - Rest Day in Missoula

Overview

Your first rest day has arrived and you’ve certainly earned it! Today is a day to relax, put up your feet, and enjoy. Benefit from a recovery stroll along the trail beside the Clark Fork River or explore the quaint downtown. This could also be the day to get some shopping done as Montana levies no state sales tax! Alternatively, catch up on some sleep, unwind, and simply get some correspondence and laundry done. Today is yours to explore, dine, and recover as you ... Your first rest day has arrived and you’ve certainly earned it! Today is a day to relax, put up your feet, and enjoy. Benefit from a recovery stroll along the trail beside the Clark Fork River or explore the quaint downtown. This could also be the day to get some shopping done as Montana levies no state sales tax! Alternatively, catch up on some sleep, unwind, and simply get some correspondence and laundry done. Today is yours to explore, dine, and recover as you please. Read More

Hotel

DoubleTree Missoula - Edgewater

Meals included

Breakfast

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (9)

Highlight of the Day

Rest day in Missoula

Enjoy some rest and relaxation or, if you are up for it, there is plenty to do from hiking to fly fishing to tubing the Clark Fork River.

Sept 1 (Labor Day) - Missoula to Helena

Overview

Saddle up! Today you'll take advantage of your well-rested legs to tackle another big ride as you continue across the fourth largest state in America. Follow the Blackfoot River out to the plains and enjoy the cool breeze as it wicks down the surrounding mountains and stirs the wildlife below. Keep a careful eye on the sky and passing fields to catch a glimpse of a bald eagle, mule deer, antelope, elk, or maybe even a grizzly bear. You'll climb to the top of Flesher... Saddle up! Today you'll take advantage of your well-rested legs to tackle another big ride as you continue across the fourth largest state in America. Follow the Blackfoot River out to the plains and enjoy the cool breeze as it wicks down the surrounding mountains and stirs the wildlife below. Keep a careful eye on the sky and passing fields to catch a glimpse of a bald eagle, mule deer, antelope, elk, or maybe even a grizzly bear. You'll climb to the top of Flesher Pass at 6,131 feet before enjoying a gradual descent into Montana's capital city for the evening. Read More

Hotel

DoubleTree Helena - Downtown

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Missoula, MT to Helena, MT - Approximately 116 mi | 187 km and 4,961 ft | 1,512 m

Sept 2 - Helena to Three Forks

Overview

Another picturesque day of riding awaits as you work your way south through Big Sky Country. You'll end up in Three Forks, near where the Jefferson, Gallatin, and Madison rivers converge to form the Missouri River. Sacajawea, who was interpreter and guide for Lewis and Clark, was kidnapped near here as a child and recognized it as her homeland when the explorers arrived here in 1805. Tonight, you'll stay at the historic Sacajawea Hotel.

Hotel

Sacajawea Hotel

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (10)

Highlight of the Day

Stay at the charming Sacajawea Hotel

Originally built in 1910, the hotel was restored in 2009 by the Folkvord family, who runs it today.

Ride Options

Ride Option 1

TODAY'S RIDE:

Helena, MT to Three Forks, MT - Approximately 88 mi | 142 km and 3,491 ft | 1,064 m

Sept 3 - Three Forks to Bozeman

Overview

Today is a relatively short ride into Bozeman, which gives you an opportunity to enjoy this happening town. As you reach your day's destination, glance east to the Bridger and Bangtail Mountain ranges. These two ranges, separated by Bridger Canyon, were once home to a pair of bickering brothers who pastured horses. Their constant quarreling over which horses belonged to whom made one brother decide to "bang," or cut short, his horse's tails to identify them, and so ... Today is a relatively short ride into Bozeman, which gives you an opportunity to enjoy this happening town. As you reach your day's destination, glance east to the Bridger and Bangtail Mountain ranges. These two ranges, separated by Bridger Canyon, were once home to a pair of bickering brothers who pastured horses. Their constant quarreling over which horses belonged to whom made one brother decide to "bang," or cut short, his horse's tails to identify them, and so the name was born. Enjoy lunch on your own when you arrive, then the afternoon is yours to explore from our home base in the heart of town. Dinner is also on your own this evening. Read More

Hotel

The Lark

Meals included

Breakfast

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (11)

Highlight of the Day

Explore Bozeman

Ride into the heart of Bozeman and enjoy the day exploring this gem of the West.

Ride Options

Ride Option 1

TODAY'S RIDE:

Three Forks, MT to Bozeman, MT - Approximately 43 mi | 69 km and 1,369 ft | 417 m

Sept 4 - Bozeman to Columbus

Overview

Today's big ride takes you along the Yellowstone River and the northern border of Yellowstone National Park. Continue to soak up the majestic peaks and rolling fields of the Rocky Mountains on your last full day in Montana. At this point you are surrounded by six different mountain ranges including Beartooth Mountain Range—home to the highest peak in the state, Granite Peak (12,799 ft).

Hotel

Super 8

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Bozeman, MT to Columbus, MT - Approximately 109 mi | 175 km and 2,718 ft | 828 m

Sept 5 - Columbus to Lovell

Overview

Travel south this morning to bid farewell to Montana and cross the border into your fifth state: Wyoming. After passing over the Yellowstone River and departing the fisherman's paradise of Columbus, you will begin to discover the second-least densely populated state in the United States. Don't let these grasslands deceive you though: wildlife such as bald eagles, buffalo, and antelope abound in this area of the Wild West. End your day by crossing the Shoshone River ... Travel south this morning to bid farewell to Montana and cross the border into your fifth state: Wyoming. After passing over the Yellowstone River and departing the fisherman's paradise of Columbus, you will begin to discover the second-least densely populated state in the United States. Don't let these grasslands deceive you though: wildlife such as bald eagles, buffalo, and antelope abound in this area of the Wild West. End your day by crossing the Shoshone River and settling in at the foot of the Bighorn Mountains at the newly remodeled Horseshoe Bend Motel. Tonight, enjoy a hearty meal from The Bull Pub restaurant as you prepare yourself for tomorrow's big climb. Read More

Hotel

Horseshoe Bend Motel | Cattlemen Motel

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (12)

Highlight of the Day

Celebrate State #5: Wyoming

Transition into another new state as you ride through the endless meadows and farmland encountering more cows than cars.

Ride Options

Ride Option 1

TODAY'S RIDE:

Columbus, MT to Lovell, WY - Approximately 90 mi | 144 km and 2,627 ft | 800 m

Sept 6 - Lovell to Sheridan

Overview

Today promises to be a memorable and momentous day, as you will ascend to Observation Point, which, at 9,430 feet, is the highest point of your epic journey. The morning will begin with a leisurely 20 miles of warm-up terrain. Look for the pelicans as you cross the Bighorn River, and get ready to start the toughest climb of the trip. The path you will follow, known as “The Medicine Wheel Passage,” twists up, up, and up for 20 miles (and plenty of double-digit gr... Today promises to be a memorable and momentous day, as you will ascend to Observation Point, which, at 9,430 feet, is the highest point of your epic journey. The morning will begin with a leisurely 20 miles of warm-up terrain. Look for the pelicans as you cross the Bighorn River, and get ready to start the toughest climb of the trip. The path you will follow, known as “The Medicine Wheel Passage,” twists up, up, and up for 20 miles (and plenty of double-digit gradients) through the Bighorn National Forest. Take a moment to congratulate yourself at the top and be sure to get a photo at Observation Point with your bike over your head — you've earned it! Enjoy the views of the high mountain meadows as you continue on and keep your eyes peeled for marmots, moose, and bighorn sheep. After another delicious picnic lunch hosted by your guides, enjoy the sweeping, picturesque descent into the quintessential ranching town of Sheridan. Read More

Hotel

Historic Sheridan Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (13)

Highlight of the Day

Tackle the famous climb up Big Horn Pass

Today is the "Queen Stage" of the trip as you climb over 20 miles (32 km) to Observation Point.

Ride Options

Ride Option 1

TODAY'S RIDE:

Lovell, WY to Sheridan, WY - Approximately 99 mi | 159 km and 7,732 ft | 2,356 m

Sept 7 - Sheridan to Gillette

Overview

As you pedal away from Sheridan, it's easy to imagine the Old West battles and shootouts that once took place here. In fact, just north of here is the site of the Battle of the Little Bighorn where General Custer was killed. Ride like the wind through the vast open countryside, but don't blink as you pass Spotted Horse (Population: 2). In fact, be sure to stop in at the Spotted Horse Bar for a co*ke and a photo op. Then press onward and you'll find yourself in Gillet... As you pedal away from Sheridan, it's easy to imagine the Old West battles and shootouts that once took place here. In fact, just north of here is the site of the Battle of the Little Bighorn where General Custer was killed. Ride like the wind through the vast open countryside, but don't blink as you pass Spotted Horse (Population: 2). In fact, be sure to stop in at the Spotted Horse Bar for a co*ke and a photo op. Then press onward and you'll find yourself in Gillette, also known as the "Energy Capital of the Nation," home to plenty of natural resources that made this town a center of the oil and gas industry. With views of Eagle Butte Mine along the way, you can see some of the pits from which Wyoming supplies 35% of the nation's coal. Read More

Hotel

Hampton Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (14)

Highlight of the Day

Spotted Horse

Stop and meet the two residents in this tiny "town".

Ride Options

Ride Option 1

TODAY'S RIDE:

Sheridan, WY to Gillette, WY - Approximately 108 mi | 173 km and 4,753 ft | 1,448 m

Sept 8 - Gillette to Spearfish

Overview

Today's ride takes you past Devil's Tower, declared America's first National Monument by Teddy Roosevelt in 1906. This stump-shaped volcanic formation was formed from hot magma 40 million years ago and measures 867 feet from base to summit. The sediment around it has eroded away, leaving the tower you see today. It is near the Bear Lodge Mountains in the Black Hills and is a sacred place among several Native American tribes. Legend has it that several young Native A... Today's ride takes you past Devil's Tower, declared America's first National Monument by Teddy Roosevelt in 1906. This stump-shaped volcanic formation was formed from hot magma 40 million years ago and measures 867 feet from base to summit. The sediment around it has eroded away, leaving the tower you see today. It is near the Bear Lodge Mountains in the Black Hills and is a sacred place among several Native American tribes. Legend has it that several young Native American girls who were being chased by bears, climbed up on a rock to escape and were saved by the Great Spirit who raised the rock high into the sky. The angry bears could not reach the top but left deep claw marks in the sides of the tower trying. Indeed, the tower is formed by columns of rock that resemble claw marks. The columns and cracks make it an attractive site for rock climbers, and one last fun fact, it was featured in Steven Spielberg's Close Encounters of the Third Kind in 1977. Be sure to stop for a photo as you pass by. You'll continue through the hills as you make your way to Sundance. This town may ring a bell, as it is where "The Sundance Kid" got his name after being released from jail here. Notice his statue near the courthouse on the town square and the Crook County Museum where his trial took place. As you leave Sundance, it's only a few more miles until you cross the border into South Dakota, state number six. Tonight's home is in the small town of Spearfish, so named for the crystal clear waters of Spearfish Creek, where Native Americans would hunt fish with spears. After checking in at the Best Western, take a stroll to Main Street and enjoy dinner on your own this evening. Read More

Hotel

Best Western

Meals included

Breakfast | Lunch

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (15)

Highlight of the Day

Enter State #6 and ride by Devil's Tower

This stump-shaped volcanic formation was America's first National Monument.

Ride Options

Ride Option 1

TODAY'S RIDE:

Gillette, WY to Spearfish, SD - Approximately 108 mi | 174 km and 4,779 ft | 1,457 m

Sept 9 - Spearfish to Rapid City

Overview

Today's ride features the Black Hills of South Dakota. As you ride among the Ponderosa pines of this region, you will discover how the hills received their name. These trees absorb so much of the light, they make the area look practically black. This is another challenging but gorgeous day of riding. You'll begin with a serene and scenic climb up Spearfish Canyon, one of the most stunning canyons in America. It has been formed by erosion over 5 million years and is ... Today's ride features the Black Hills of South Dakota. As you ride among the Ponderosa pines of this region, you will discover how the hills received their name. These trees absorb so much of the light, they make the area look practically black. This is another challenging but gorgeous day of riding. You'll begin with a serene and scenic climb up Spearfish Canyon, one of the most stunning canyons in America. It has been formed by erosion over 5 million years and is said to be 12 times older than the Grand Canyon. The final scenes of "Dances with Wolves" were filmed here. As you leave the canyon, you'll continue climbing up to the gold mining town of Lead, home to the Homestake Gold Mine. Before it closed in 2002, it was the largest, deepest mine in North America. You'll pass by the Visitor Center, so be sure to stop for a snack and take a look. From here, you'll have another big effort as you work your way through the hills to Roubaix and then descend into Rapid City for your second well-deserved rest day. Read More

Hotel

Hotel Alex Johnson

Meals included

Breakfast | Lunch | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (16)

Highlight of the Day

Climb through Spearfish Canyon

Savor stunning vistas and look for the resident mountain goats as you pass Bridal Veil Falls.

Ride Options

Ride Option 1

TODAY'S RIDE:

Spearfish, SD to Rapid City, SD - Approximately 74 mi | 119 km and 5,201 ft | 1,585 m

Sept 10 - Rest Day in Rapid City

Overview

Your second rest day is here! Today is your day to rest, recover, and celebrate that your hard work has now taken you across 40% of the country! Activities abound to occupy your time in Rapid City. Take this opportunity to visit the eye-catching Mount Rushmore National Monument and Crazy Horse Monument. Or maybe stay closer to town and check out the enormous sculptures at Dinosaur Park, walk the imaginative Art Alley, or perhaps quiz each other on the Presidential s... Your second rest day is here! Today is your day to rest, recover, and celebrate that your hard work has now taken you across 40% of the country! Activities abound to occupy your time in Rapid City. Take this opportunity to visit the eye-catching Mount Rushmore National Monument and Crazy Horse Monument. Or maybe stay closer to town and check out the enormous sculptures at Dinosaur Park, walk the imaginative Art Alley, or perhaps quiz each other on the Presidential statues located on the street corners of downtown. Whatever you do, don't forget to kick back for a time and enjoy your accomplishments on reaching this milestone! Read More

Hotel

Hotel Alex Johnson

Meals included

Breakfast

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (17)

Highlight of the Day

Rest Day in Rapid City

It’s a short drive to the Black Hills where you can visit Mt Rushmore, the Crazy Horse Memorial, Sylvan Lake, Custer State Park, and more!

Sept 11 - Rapid City to Kadoka

Overview

Back in the saddle and well-rested, today you will venture into Wall, SD, home of the famous Wall Drug, a strip mall consisting of restaurants, gift shops, and drug stores. You can't miss it, as you undoubtedly have seen billboards for "5 cent coffee" for several days now. Please note that today includes a stretch of three miles and another of 25 miles on Interstate 90 before reaching Wall. While we strive to avoid interstate riding, it is unavoidable due to the nat... Back in the saddle and well-rested, today you will venture into Wall, SD, home of the famous Wall Drug, a strip mall consisting of restaurants, gift shops, and drug stores. You can't miss it, as you undoubtedly have seen billboards for "5 cent coffee" for several days now. Please note that today includes a stretch of three miles and another of 25 miles on Interstate 90 before reaching Wall. While we strive to avoid interstate riding, it is unavoidable due to the nature of the roads in this area. You may certainly opt to shuttle these sections. After a picnic (and a stop at Wall Drug, of course), you will ride into Badlands National Park. This area is a gold mine for fossil discoveries, and findings of new species that once roamed this region is not unheard of. The landscape is extremely delicate, ever changing. It was used by many Native Americans as hunting grounds as well as a place to live, with the higher areas perfect as lookouts to see oncoming enemies or herds of animals. Take your time and soak up the scenery as you wind your way through this unparalleled land of buttes and spires. Be sure to look for antelope, pronghorns, and big horn sheep as you pedal through the park. Read More

Hotel

America’s Best Value Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (18)

Highlight of the Day

Ride through Badlands National Park

Experience the wonder of the Badlands, a unique landscape that seems to pop up out of nowhere along your ride.

Ride Options

Ride Option 1

TODAY'S RIDE:

Rapid City, SD to Kadoka, SD - Approximately 113 mi | 181 km and 4,014 ft | 1,223 m

Sept 12 - Kadoka to Oacoma

Overview

Today you leave the gateway to the Badlands and continue your journey across the grasslands of South Dakota. This area, including Fort Pierre National Grasslands, provides visitors excellent opportunities to camp, hunt, and fish, but for you it provides a steady, straight road past glowing fields of sunflowers and picturesque farms en route to your destination of Oacoma, South Dakota. You'll spend the night at Arrowwood Resort, located next to the Missouri River.

Hotel

Arrowwood Resort at Cedar Shore

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (19)

Highlight of the Day

Appreciate a change in scenery

Find beauty in the open spaces as you find your groove and just ride.

Ride Options

Ride Option 1

TODAY'S RIDE:

Kadoka, SD to Oacoma, SD - Approximately 115 mi | 185 km and 3,334 ft | 1,016 m

Sept 13 - Oacoma to Mitchell

Overview

There are two big reasons to celebrate today: you only have to ride 76 miles, and even better, you have pedaled halfway across the United States! Take some time to reflect on your journey thus far as you cross the rushing Missouri River and head into another beautiful day of open grasslands. Relax as you spin your way through these lands that were once occupied by early American settlers working on the railroad, farms, ranches, and in the fur trade. And if your legs... There are two big reasons to celebrate today: you only have to ride 76 miles, and even better, you have pedaled halfway across the United States! Take some time to reflect on your journey thus far as you cross the rushing Missouri River and head into another beautiful day of open grasslands. Relax as you spin your way through these lands that were once occupied by early American settlers working on the railroad, farms, ranches, and in the fur trade. And if your legs will allow it, take a short detour and check out Mitchell's biggest attraction: The Corn Palace! Read More

Hotel

Hampton Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (20)

Highlight of the Day

Celebrate the Halfway Mark

Today you reach the halfway point of your journey. After the ride, you can visit Mitchell’s claim to fame, the World's Only Corn Palace.

Ride Options

Ride Option 1

TODAY'S RIDE:

Oacoma, SD to Mitchell, SD - Approximately 76 mi | 122 km and 1,073 ft | 327 m

Sept 14 - Mitchell to Sioux Falls

Overview

At 72 miles, today is another relatively short day in the saddle. Your ride brings you into South Dakota's largest city: Sioux Falls. The location of Sioux Falls, on the banks of the cascading Big Sioux River, has been a site of human habitation since antiquity. This area was first settled by Native Americans who harnessed the water source for agriculture. The land near the water was also held sacred as a burial ground and is still respected as such today. This even... At 72 miles, today is another relatively short day in the saddle. Your ride brings you into South Dakota's largest city: Sioux Falls. The location of Sioux Falls, on the banks of the cascading Big Sioux River, has been a site of human habitation since antiquity. This area was first settled by Native Americans who harnessed the water source for agriculture. The land near the water was also held sacred as a burial ground and is still respected as such today. This evening, after enjoying dinner on your own, take a stroll along the river to Falls Park. Read More

Hotel

Holiday Inn City Centre

Meals included

Breakfast | Lunch

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Mitchell, SD to Sioux Falls, SD - Approximately 73 mi | 117 km and 1,453 ft | 443 m

Sept 15 - Sioux Falls to Fairmont

Overview

Today you’ll bid a fond farewell to South Dakota at mile 16 as you cross the border into Minnesota, the seventh state along your route so far. Today is the longest ride of the trip at 126 miles and it’s predominantly flat, so hope for a tailwind. By popular request, we are by-passing the cornfields of Iowa this year and routing you through Minnesota, aka The Land of 10,000 Lakes. You’ll count a few of them today as you break for a picnic near the shore of Lake... Today you’ll bid a fond farewell to South Dakota at mile 16 as you cross the border into Minnesota, the seventh state along your route so far. Today is the longest ride of the trip at 126 miles and it’s predominantly flat, so hope for a tailwind. By popular request, we are by-passing the cornfields of Iowa this year and routing you through Minnesota, aka The Land of 10,000 Lakes. You’ll count a few of them today as you break for a picnic near the shore of Lake Okabena in Worthington, pedal past Temperance Lake near Sherburn and end your ride in Fairmont after passing by Budd Lake. Logistics are simple tonight – dine at the hotel restaurant and spend the rest of your time focusing on recovery. Read More

Hotel

Best Western

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (21)

Highlight of the Day

Enter Minnesota: State #7

Ride past Falls Park and bid farewell to South Dakota as you enter Minnesota.

Ride Options

Ride Option 1

TODAY'S RIDE:

Sioux Falls, SD to Fairmont, MN - Approximately 126 mi | 202 km and 2,070 ft | 636 m

Sept 16 - Fairmont to Austin

Overview

Did you know, in addition to Scotch tape, that Masking tape, Bisquick, Wheaties, and Green Giant vegetables were invented in Minnesota? Well, today is your chance to get a commemorative photo with the Jolly Green Giant himself. The 55.5 feet tall statue was commissioned by Paul Hedberg in 1978. Hedberg, the owner of a local radio station and host of a show called “Welcome Travelers”, gave each of his guests Green Giant vegetables from the local factory as a part... Did you know, in addition to Scotch tape, that Masking tape, Bisquick, Wheaties, and Green Giant vegetables were invented in Minnesota? Well, today is your chance to get a commemorative photo with the Jolly Green Giant himself. The 55.5 feet tall statue was commissioned by Paul Hedberg in 1978. Hedberg, the owner of a local radio station and host of a show called “Welcome Travelers”, gave each of his guests Green Giant vegetables from the local factory as a parting gift. When he learned that I-90 would bypass Blue Earth, he feared he would lose his supply of travelers so he took it upon himself to raise money for the statue in hopes that it would lure tourists to town. While Green Giant no longer owns the local canning plant and the radio show no longer exists, the town’s beloved statue still stands and has spawned a Giant Museum and Giant Days festival. If that’s not enough Americana for you today, be sure to visit the Spam Museum when you get to Austin. Read More

Hotel

Holiday Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (22)

Highlight of the Day

Jolly Green Giant

Get a commemorative photo with the Jolly Green Giant.

Ride Options

Ride Option 1

TODAY'S RIDE:

Fairmont, MN to Austin, MN - Approximately 81 mi | 130 km and 1,523 ft | 464 m

Sept 17 - Austin to La Crosse

Overview

This morning, say goodbye to the home of Hormel as you make your way across the rest of southern Minnesota. Once again, the ride today is long and relatively flat. The highlight comes about halfway through when you enter the Root River Trail. Enjoy 40 miles of paved bike path as you meander through small towns set on the banks of the Root River. As the path ends, you’ll get a wake-up call in the form of a steep one-mile climb. After a few miles on the plateau, you... This morning, say goodbye to the home of Hormel as you make your way across the rest of southern Minnesota. Once again, the ride today is long and relatively flat. The highlight comes about halfway through when you enter the Root River Trail. Enjoy 40 miles of paved bike path as you meander through small towns set on the banks of the Root River. As the path ends, you’ll get a wake-up call in the form of a steep one-mile climb. After a few miles on the plateau, you’ll descend toward the mighty Mississippi River and the border of state number eight: good ol’ Wisconsin. Our home for tonight is The Charmant Hotel, a boutique hotel housed in a renovated candy factory. The name was inspired by a premium line of chocolates once made here. The maple flooring, wooden beams, and exposed brick of the original 1898 structure have been preserved, giving this historic hotel a warm, charming appeal. Enjoy the lovely setting with a drink on the rooftop terrace or take a stroll through the park to the bank of the mighty Mississippi River. Dinner tonight is on your own in this charming town of La Crosse. Read More

Hotel

The Charmant Hotel

Meals included

Breakfast | Lunch

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (23)

Highlight of the Day

Enter State #8 and cozy up at The Charmant Hotel

Enjoy your stay in this candy factory turned boutique hotel.

Ride Options

Ride Option 1

TODAY'S RIDE:

Austin, MN to La Crosse, WI - Approximately 117 mi | 188 km and 2,890 ft | 880 m

Sept 18 - La Crosse to Spring Green

Overview

Gear up! Today’s ride is anything but flat! You’ll cross the heart of Wisconsin's Driftless Area today. This unglaciated region will surprise and delight you with its diversity. Forested slopes give way to green valleys and dramatic limestone bluffs that have been carved through the ages by crystal clear trout streams. Today hosts the perfect opportunities to cool yourself down with a few splashes from one of the many cold water steams. Enjoy a hearty picnic lun... Gear up! Today’s ride is anything but flat! You’ll cross the heart of Wisconsin's Driftless Area today. This unglaciated region will surprise and delight you with its diversity. Forested slopes give way to green valleys and dramatic limestone bluffs that have been carved through the ages by crystal clear trout streams. Today hosts the perfect opportunities to cool yourself down with a few splashes from one of the many cold water steams. Enjoy a hearty picnic lunch mid-ride before forging on toward the quaint town of Spring Green. You will pass Frank Lloyd Wright's famous home, Taliesin, on your way to our home for the evening. Kick back with a post-ride beer by the fire pit. Tonight, you can relax and enjoy a well-earned dinner at our hotel. Read More

Hotel

Spring Valley Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (24)

Highlight of the Day

Ride across the Driftless Region

Conquer everything from rollers to short but surprisingly steep hills as you navigate this cycling paradise.

Ride Options

Ride Option 1

TODAY'S RIDE:

La Crosse, WI to Spring Green, WI - Approximately 104 mi | 167 km and 4,576 ft | 1,397 m

Sept 19 - Spring Green to Madison

Overview

Today’s ride is shorter, but jam-packed with great roads. It’s a favorite route of the local Trek Travel team. You’ll sweep through the last hills of the Driftless Area en route to more mellow terrain. Many of the farms you will see along the way are organic and use sustainable growing practices to produce a wide variety of heirloom vegetables and artisanal cheeses found in many of Madison’s restaurants and at its bountiful farmer’s market. Finish this leg... Today’s ride is shorter, but jam-packed with great roads. It’s a favorite route of the local Trek Travel team. You’ll sweep through the last hills of the Driftless Area en route to more mellow terrain. Many of the farms you will see along the way are organic and use sustainable growing practices to produce a wide variety of heirloom vegetables and artisanal cheeses found in many of Madison’s restaurants and at its bountiful farmer’s market. Finish this leg strong as you make your way around Lake Mendota and roll into Wisconsin's gorgeous capital city. Enjoy a picnic lunch on the lawn of the Capitol before we check-in. Then relax and prepare to celebrate with a special evening in Trek Travel's midwestern hometown! Read More

Hotel

Hotel Indigo

Meals included

Breakfast | Lunch | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (25)

Highlight of the Day

Welcome to Trek Travel’s hometown

You'll be greeted by our Trek Travel Team as we welcome you home for the next two nights.

Ride Options

Ride Option 1

TODAY'S RIDE:

Spring Green, WI to Madison, WI - Approximately 54 mi | 87 km and 2,476 ft | 755 m

Sept 20 - Rest Day in Madison

Overview

Congrats on reaching your third rest day! You are now two thirds of the way through the total mileage and elevation of this epic conquest. Today is your day to explore Wisconsin's thriving capital city. Madison has lots to offer when it comes to food, the arts, entertainment, and recreational activities. Tour the Capitol building and don't miss a stroll down State Street, the pedestrian-only street connecting the Capitol to the University of Wisconsin. Have a beer a... Congrats on reaching your third rest day! You are now two thirds of the way through the total mileage and elevation of this epic conquest. Today is your day to explore Wisconsin's thriving capital city. Madison has lots to offer when it comes to food, the arts, entertainment, and recreational activities. Tour the Capitol building and don't miss a stroll down State Street, the pedestrian-only street connecting the Capitol to the University of Wisconsin. Have a beer at Memorial Union Terrace, a favorite local hangout on the shore of Lake Mendota. Notice the spectacle of more bikes than cars in many sections of town and the plentiful variety of local breweries and outdoor patios for dining. You may also choose to squeeze in a yoga class or a paddle on one of the lakes. Kick back and relax however you see fit — today is your day off. Read More

Hotel

Hotel Indigo

Meals included

Breakfast

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (26)

Highlight of the Day

Explore downtown Madison

Take a free tour of the beautiful Capitol building while you are in town.

Sept 21 - Madison to Milwaukee

Overview

Another great day stretches out ahead of you, as you exit Madison via a popular bike path and ease back into small towns and rolling farmland. Enjoy roaming alongside the scattered lakes and quiet suburbs as you near Milwaukee. The city is famous for breweries including Pabst, Schlitz, Blatz, and Miller to name but a few, started by an influx of German immigrants in the mid 19th century. You might also remember the sitcoms Happy Days and Laverne & Shirley, and of co... Another great day stretches out ahead of you, as you exit Madison via a popular bike path and ease back into small towns and rolling farmland. Enjoy roaming alongside the scattered lakes and quiet suburbs as you near Milwaukee. The city is famous for breweries including Pabst, Schlitz, Blatz, and Miller to name but a few, started by an influx of German immigrants in the mid 19th century. You might also remember the sitcoms Happy Days and Laverne & Shirley, and of course this is the birthplace of Harley-Davidson motorcycles. You'll get a taste of its history as you ride past the home of the Milwaukee Brewers and the Harley-Davidson museum before arriving at the Iron Horse Hotel. Try your hand at a game of pool or have a drink in The Yard as you savor your short time at this striking warehouse turned hotel. We will enjoy dinner here as well. Read More

Hotel

The Iron Horse Hotel

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Madison WI, to Milwaukee, WI - Approximately 86 mi | 138 km and 2,116 ft | 645 m

Sept 22 - Milwaukee to Holland

Overview

Enjoy a leisurely morning before your short ride to the Lake Express ferry terminal. In only two-and-a-half hours this high-speed ferry will take you across the grand waters of Lake Michigan. Upon arrival on the eastern shore, you will be on Eastern Time and enter the ninth state of your journey: Michigan. Feel the lakeside air as you ride south to the Dutch-inspired city of Holland. In fact it's known for Tulip Time, a Dutch Heritage festival that has been taking p... Enjoy a leisurely morning before your short ride to the Lake Express ferry terminal. In only two-and-a-half hours this high-speed ferry will take you across the grand waters of Lake Michigan. Upon arrival on the eastern shore, you will be on Eastern Time and enter the ninth state of your journey: Michigan. Feel the lakeside air as you ride south to the Dutch-inspired city of Holland. In fact it's known for Tulip Time, a Dutch Heritage festival that has been taking place for over 90 years featuring millions of tulips, Klompen dancing, wooden shoe carving, and much more. Your visit will be short but sweet as you'll reach the hotel right around dinner time. Read More

Hotel

Holiday Inn Express

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (27)

Highlight of the Day

Cross Lake Michigan and enter State #9.

Skip the Chicago traffic and take the ferry across the lake. Say hello to Michigan!

Ride Options

Ride Option 1

TODAY'S RIDE:

Milwaukee, WI to Holland, MI - Approximately 40 mi | 64 km and 695 ft | 214 m

Sept 23 - Holland to Marshall

Overview

Today you will zigzag your way southeast through the open countryside and farms of lower Michigan. Enjoy another fabulous picnic prepared by your guides at a perfectly situated park in Prairieville Township. If you are a car fanatic, be sure to stop at the Gilmore Automobile Museum, which you'll pass just after lunch. Your path will continue to meander its way past the outskirts of Battle Creek to the town of Marshall – home to some interesting places such as the ... Today you will zigzag your way southeast through the open countryside and farms of lower Michigan. Enjoy another fabulous picnic prepared by your guides at a perfectly situated park in Prairieville Township. If you are a car fanatic, be sure to stop at the Gilmore Automobile Museum, which you'll pass just after lunch. Your path will continue to meander its way past the outskirts of Battle Creek to the town of Marshall – home to some interesting places such as the Honolulu House, The American Museum of Magic, and our favorite, the Dark Horse Brewery. Read More

Hotel

Holiday Inn Express

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Holland, MI to Marshall, MI - Approximately 92 mi | 148 km and 2,499 ft | 762 m

Sept 24 - Marshall to Rossford

Overview

Gear up for a big ride today! Today’s ride will have you pedaling in a variety of settings from quiet farm fields to the suburban community of Rossford. After weaving through the small towns and lakes of southeastern Michigan, drop into Ohio, the 10th state of your journey. We break for lunch at a favorite local spot, Randy’s BBQ. After some mouth-watering hickory smoked barbecue, we pedal ten miles on the quiet, smooth blacktop of the Falling Waters Trail befor... Gear up for a big ride today! Today’s ride will have you pedaling in a variety of settings from quiet farm fields to the suburban community of Rossford. After weaving through the small towns and lakes of southeastern Michigan, drop into Ohio, the 10th state of your journey. We break for lunch at a favorite local spot, Randy’s BBQ. After some mouth-watering hickory smoked barbecue, we pedal ten miles on the quiet, smooth blacktop of the Falling Waters Trail before reaching our home for tonight in the outskirts of Toledo. Read More

Hotel

Hampton Inn Toledo-Perrysburg

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Marshall, MI to Rossford, OH - Approximately 120 mi | 193 km and 1,939 ft | 594 m

Sept 25 - Rossford to Oberlin

Overview

Today is the last “flat” day of riding on this trip! The majority of our ride is on the North Coast Inland Trail bike path, which was built on the abandoned Toledo, Norwalk and Cleveland Railroad. The railroad was constructed in 1851 serving as a vital link between Chicago and Cleveland and leading to the founding of many of the small towns you will pass through on today's ride. We will end our ride in the college town of Oberlin, where we’ll enjoy a night at ... Today is the last “flat” day of riding on this trip! The majority of our ride is on the North Coast Inland Trail bike path, which was built on the abandoned Toledo, Norwalk and Cleveland Railroad. The railroad was constructed in 1851 serving as a vital link between Chicago and Cleveland and leading to the founding of many of the small towns you will pass through on today's ride. We will end our ride in the college town of Oberlin, where we’ll enjoy a night at The Hotel at Oberlin, a modern building, yet traditionally designed LEED Platinum hotel, making it one of the most environmentally sustainable hotel projects in the U.S. Dinner will be served at 1833, the hotel’s restaurant, with its socially conscious menus using ingredients from local farmers. After dinner, it’s a short walk to the local ice cream shop. We recommend enjoying your second dessert (you’ve earned it) as you stroll through the historic Tappan Square. Read More

Hotel

The Hotel at Oberlin

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Rossford, OH to Oberlin, OH - Approximately 87 mi | 140 km and 1,190 ft | 362 m

Sept 26 - Oberlin to Newbury

Overview

The hills gradually pick up today as we pass through acres of farmland before dropping down to the Cuyahoga River and riding through Cuyahoga Valley National Park. From here, it won't be long before you'll be sharing the road with the horse-drawn buggies of the local Amish population. Today's ride ends in Geauga County, home to the world's fourth largest Amish community. We'll soak it all in as we settle in for the night at an English Tudor-style lodge in Punderson ... The hills gradually pick up today as we pass through acres of farmland before dropping down to the Cuyahoga River and riding through Cuyahoga Valley National Park. From here, it won't be long before you'll be sharing the road with the horse-drawn buggies of the local Amish population. Today's ride ends in Geauga County, home to the world's fourth largest Amish community. We'll soak it all in as we settle in for the night at an English Tudor-style lodge in Punderson State Park. Read More

Hotel

Punderson Manor Lodge

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (28)

Highlight of the Day

Ride through Cuyahoga Valley National Park

Ride through Cuyahoga Valley National Park and alongside horse drawn buggies in Amish Country.

Ride Options

Ride Option 1

TODAY'S RIDE:

Oberlin, OH to Newbury, OH - Approximately 80 mi | 129 km and 3,625 ft | 1,105 m

Sept 27 - Newbury to Meadville

Overview

Find yourself in rolling terrain today as you cruise through northeastern Ohio on your way to your 11th state of Pennsylvania. This comparatively short ride will allow you to rest up for the string of four centuries to follow. Be sure to stop and see the carp at the spillway at Pymatuning Reservoir. The fish are so plentiful, that ducks can walk on their backs. We kid you not.

Hotel

Holiday Inn Express

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Enter State #11: Pennsylvania

Ride Options

Ride Option 1

TODAY'S RIDE:

Newbury, OH to Meadville, PA - Approximately 64 mi | 103 km and 2,307 ft | 703 m

Sept 28 - Meadville to Bradford

Overview

Today's ride continues through an area noted for its Amish communities. Amish people are known for valuing simplicity, emphasizing family and community, and for their separation from the modern world including amenities such as electricity (although some groups have become more liberal in their views and practices). The riding continues to be challenging through these rolling hills but the lush, serene countryside is sure to boost your mood and your spirits as you n... Today's ride continues through an area noted for its Amish communities. Amish people are known for valuing simplicity, emphasizing family and community, and for their separation from the modern world including amenities such as electricity (although some groups have become more liberal in their views and practices). The riding continues to be challenging through these rolling hills but the lush, serene countryside is sure to boost your mood and your spirits as you near the east coast. Today culminates in a ride along the Allegheny River, past the impressive Kinzua Dam, and through the beautiful foliage of the Allegheny National Forest. Read More

Hotel

Holiday Inn Express

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (29)

Highlight of the Day

Experience the foliage of the Allegheny National Forest

See what the East has to offer through the peaceful rolling hills and past the impressive Kinzua Dam along the Allegheny River.

Ride Options

Ride Option 1

TODAY'S RIDE:

Meadville, PA to Bradford, PA - Approximately 101 mi | 162 km and 5,450 ft | 1,662 m

Sept 29 - Bradford to Corning

Overview

Before you leave today make sure you pick up a commemorative Zippo lighter straight from the town where it all started. Then you'll head out to cross the border into number 12: New York! Settle in for a scenic but challenging ride full of ups and downs as you head to Corning today, which many will know for its manufacture of glass and ceramic products by Corning Incorporated, as well as being recognized as a top 25 small-city art destination.

Hotel

Hilton Garden Inn Corning Downtown

Meals included

Breakfast | Lunch | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (30)

Highlight of the Day

Enter State #12: New York

Enjoy more of the rolling hills as you make your way towards your fourth and final rest day of the trip.

Ride Options

Ride Option 1

TODAY'S RIDE:

Bradford, PA to Corning, NY - Approximately 102 mi | 164 km and 4,602 ft | 1,403 m

Sept 30 - Rest Day in Corning

Overview

Awake to your final rest day in the Crystal City. Linger over that cup of coffee as you reflect on how far you've come. Only a tad over 500 miles remain on this epic journey of yours! But today is yours to relax. Stroll along the banks of the Chemung River or visit the Corning Museum of Glass or the Rockwell Museum of Western Art. Take some time to explore the historic downtown with its many galleries, shops, and restaurants. You can also use this day to get your la... Awake to your final rest day in the Crystal City. Linger over that cup of coffee as you reflect on how far you've come. Only a tad over 500 miles remain on this epic journey of yours! But today is yours to relax. Stroll along the banks of the Chemung River or visit the Corning Museum of Glass or the Rockwell Museum of Western Art. Take some time to explore the historic downtown with its many galleries, shops, and restaurants. You can also use this day to get your last stash of clean clothes ready, check your emails, and bring friends and family back home up to speed on your adventures so far! Read More

Hotel

Hilton Garden Inn Corning Downtown

Meals included

Breakfast

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (31)

Highlight of the Day

Visit the Corning Museum of Glass

Watch a glass-blowing demonstration, even partake in blowing a piece of your own, and learn about the many uses of glass at this renowned mu... Watch a glass-blowing demonstration, even partake in blowing a piece of your own, and learn about the many uses of glass at this renowned museum. Read More

Oct 1 - Corning to Cazenovia

Overview

Today you'll ride north through New York's famous Finger Lakes Region where you'll catch glimpses of Seneca Lake and the rugged cliffs above. Watkins Glen at the south end of the lake is not only known for its picturesque views and water activities, but also for its street car racing. Tonight, you'll stay at the historic Brewster Inn on the shore of Lake Cazenovia. You'll enjoy dinner in their award winning restaurant. It's the perfect place to reminisce about the h... Today you'll ride north through New York's famous Finger Lakes Region where you'll catch glimpses of Seneca Lake and the rugged cliffs above. Watkins Glen at the south end of the lake is not only known for its picturesque views and water activities, but also for its street car racing. Tonight, you'll stay at the historic Brewster Inn on the shore of Lake Cazenovia. You'll enjoy dinner in their award winning restaurant. It's the perfect place to reminisce about the highlights and achievements of your journey and plan for the excitement and triumphs of the days ahead. Read More

Hotel

Brewster Inn | Brae Loch Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (32)

Highlight of the Day

Ride through the Finger Lakes Region

The Finger Lakes Region is known for recreational activities, iconic waterfalls and wineries.

Ride Options

Ride Option 1

TODAY'S RIDE:

Corning, NY to Cazenovia, NY - Approximately 101 mi | 163 km and 5,569 ft | 1,697 m

Oct 2 - Cazenovia to Piseco

Overview

This morning shortly after leaving Cazenovia, you'll find yourself on a stunning descent alongside a babbling brook and waterfall. Our route also intersects with the Erie Canalway Trail, a 365-mile bike trail that follows active and historic sections of the Erie Canal. Later, you'll pedal your way into Adirondack Park. The distinctions between the Adirondacks and Rocky Mountains are easy to see, with the contrasting dome-shaped summits of the Adirondacks covered in ... This morning shortly after leaving Cazenovia, you'll find yourself on a stunning descent alongside a babbling brook and waterfall. Our route also intersects with the Erie Canalway Trail, a 365-mile bike trail that follows active and historic sections of the Erie Canal. Later, you'll pedal your way into Adirondack Park. The distinctions between the Adirondacks and Rocky Mountains are easy to see, with the contrasting dome-shaped summits of the Adirondacks covered in spruce, pine, and broad-leafed trees and the highest elevation reaching just above 5,000 feet. The riding here is really rewarding as you gradually pedal up the climbs and enjoy the accompanying views of the forest and tranquil lakes before descending to our home for tonight on the shore of Piseco Lake. Read More

Hotel

Irondequoit Inn | Oxbow Lake Motel

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (33)

Highlight of the Day

Experience the Adirondacks

Enjoy the foliage as you pedal through the lower Adirondacks region.

Ride Options

Ride Option 1

TODAY'S RIDE:

Cazenovia, NY to Piseco, NY - Approximately 92 mi | 148 km and 3,677 ft | 1,122 m

Oct 3 - Piseco to Ticonderoga

Overview

Enjoy a fabulous ride today as you work your way out of the Adirondacks and head to the historic and strategic outpost town of Ticonderoga. This is the home of Fort Ticonderoga and the point between Lake George and Lake Champlain. Battles were fought at this fort in both the French and Indian War and the Revolutionary War. And for movie fans, this fort was used to film many scenes in "The Last of The Mohicans." The scenery of this area will not disappoint.

Hotel

Best Western Plus

Meals included

Breakfast | Lunch | Dinner

Highlight of the Day

Ride Options

Ride Option 1

TODAY'S RIDE:

Piseco, NY to Ticonderoga, NY - Approximately 84 mi | 135 km and 3,968 ft | 1,209 m

Oct 4 - Ticonderoga to Hanover

Overview

It's a three state kind of day! Say goodbye to New York and enter your 13th state, Vermont, with a quick float across Lake Champlain on the Ticonderoga Ferry. Once off the ferry, it's back on the bike and into the Green Mountains for a tough but colorful day in the saddle. The climbs here are spunky, but rest assured our chosen one, Brandon Gap, is gentle compared to the other passes through these mountains–and it has a rewarding open descent. Save some energy bec... It's a three state kind of day! Say goodbye to New York and enter your 13th state, Vermont, with a quick float across Lake Champlain on the Ticonderoga Ferry. Once off the ferry, it's back on the bike and into the Green Mountains for a tough but colorful day in the saddle. The climbs here are spunky, but rest assured our chosen one, Brandon Gap, is gentle compared to the other passes through these mountains–and it has a rewarding open descent. Save some energy because you still have more hills to conquer in the second half of this ride! You'll finish your ride across Vermont as you cross the Connecticut River and enter New Hampshire, your 14th state. Tonight you'll stay in the heart of downtown Hanover, home of Dartmouth College, where you are free to enjoy dinner on your own. Read More

Hotel

Six South Street Hotel

Meals included

Breakfast | Lunch

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (34)

Highlight of the Day

Ride three states in one day

Transition from New York to Vermont via a ferry across Lake Champlain, ride through Vermont and get a good night's rest in New Hampshire.

Ride Options

Ride Option 1

TODAY'S RIDE:

Ticonderoga, NY to Hanover, NH - Approximately 88 mi | 142 km and 5,288 ft | 1,612 m

Oct 5 - Hanover to North Conway

Overview

Today you can almost taste the end of your long and rewarding journey, but it's not over quite yet! There's one more stunning scenic byway calling your name as you traverse the White Mountains. There are three tough climbs to conquer before you enjoy a triumphant lunch at the top of Kancamagus Pass (affectionately known by the locals as "The Kanc"). You will see why many people come here to witness some of the best fall foliage in the country. And better yet, after ... Today you can almost taste the end of your long and rewarding journey, but it's not over quite yet! There's one more stunning scenic byway calling your name as you traverse the White Mountains. There are three tough climbs to conquer before you enjoy a triumphant lunch at the top of Kancamagus Pass (affectionately known by the locals as "The Kanc"). You will see why many people come here to witness some of the best fall foliage in the country. And better yet, after lunch, you get to enjoy a 25-mile descent. You have definitely earned it! If you have a sweet tooth don't miss the delicious treats waiting on the other side of the mountains at the White Mountain Cupcakery in North Conway. Read More

Hotel

Comfort Inn

Meals included

Breakfast | Lunch | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (35)

Highlight of the Day

Conquer Kancamagus Pass in the White Mountains National Forest

So close you can almost smell the salt water, today's ride tests everything you have left.

Ride Options

Ride Option 1

TODAY'S RIDE:

Hanover, NH to North Conway, NH - Approximately 97 mi | 156 km and 6,865 ft | 2,092 m

Oct 6 - Champagne toast at the Atlantic Ocean!

Overview

At last, it’s time for the final celebratory ride of this amazing journey. Today is your victory lap...your cross-country Champs-Élysées! After a few quick miles, you’ll enter Maine, your 15th and final state. We will pause to regroup and enjoy a final lunch before making the last push to the coast. As you approach the Atlantic, the coastal breeze and smell of salt water in the air will transport you back to the day you set out from Astoria to pedal your way a... At last, it’s time for the final celebratory ride of this amazing journey. Today is your victory lap...your cross-country Champs-Élysées! After a few quick miles, you’ll enter Maine, your 15th and final state. We will pause to regroup and enjoy a final lunch before making the last push to the coast. As you approach the Atlantic, the coastal breeze and smell of salt water in the air will transport you back to the day you set out from Astoria to pedal your way across the great United States. Your ride will come to an end on the beautiful sandy shoreline of Crescent Beach State Park, just a few miles south of Portland. The celebration begins here and will continue for the rest of the day! After a champagne toast and lots of photos on the beach, we will make our way to the Press Hotel in downtown Portland. Tonight we'll celebrate in style with a final social hour and gourmet feast from Union – you’ve certainly earned it! Read More

Hotel

Press Hotel

Meals included

Breakfast | Lunch | Social Hour | Dinner

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (36)

Highlight of the Day

Dip your wheel in the Atlantic Ocean

Let the celebration begin! Congratulate yourself as well as your group for conquering your quest of riding coast to coast!

Ride Options

Ride Option 1

TODAY'S RIDE:

North Conway, NH to Portland, ME - Approximately 68 mi | 109 km and 2,269 ft | 692 m

Oct 7 - Departure from Portland

Overview

A leisurely morning in Portland offers you the opportunity to revisit the triumphs and challenges of the previous 47 days as you say farewell to your comrades. This ride-of-a-lifetime has come to a close, but the friendships and memories produced by this epic journey have just begun. As you depart, we recommend flying out of Portland International Jetport (PWM) to the destination of your choice.

Meals included

Breakfast

Highlight of the Day

Ride Options

Ride Option 1

Cross Country USA: Portland to Portland Bike Tour 2025 Itinerary (2024)

References

Top Articles
Latest Posts
Article information

Author: Msgr. Refugio Daniel

Last Updated:

Views: 5612

Rating: 4.3 / 5 (74 voted)

Reviews: 89% of readers found this page helpful

Author information

Name: Msgr. Refugio Daniel

Birthday: 1999-09-15

Address: 8416 Beatty Center, Derekfort, VA 72092-0500

Phone: +6838967160603

Job: Mining Executive

Hobby: Woodworking, Knitting, Fishing, Coffee roasting, Kayaking, Horseback riding, Kite flying

Introduction: My name is Msgr. Refugio Daniel, I am a fine, precious, encouraging, calm, glamorous, vivacious, friendly person who loves writing and wants to share my knowledge and understanding with you.