Cross Country USA: Portland to Portland

East Coast


Cross Country USA: Portland to Portland

If you're ready for the bike trip—and challenge—of a lifetime, prepare to join Trek Travel on a bicycle tour that stretches from the Pacific to the Atlantic…

We are excited and proud to unveil our new epic Cross Country USA trip, developed in response to popular demand—Portland to Portland. The goal: ambitious. The distance: 3,600 miles. The training: intense. The opportunity: unrivaled. If you're ready for the bike trip—and challenge—of a lifetime, prepare to join Trek Travel on a bicycle tour that stretches from the Pacific to the Atlantic across the northern tier of this beautiful country. On this trip you'll climb more than 130,000 feet over the course of 39 riding days—all from the seat of a top of the line Trek carbon fiber road bike, the use of which is included in your trip price. Your shortest day will be 37 miles and the longest, 125 miles. You'll have four rest days, two "rolling recovery" days with mileage of 31 to 60 miles, and 15 days with mileage of 100 miles or more. Although the challenge and dedication to training is substantial, your Trek Travel guides will be with you every pedal stroke of the way, offering encouragement, mechanical and logistical support, camaraderie, and our renowned Trek Travel guest service. Our signature attention to detail—and exhaustive planning and provisioning—will leave you free to just ride. You'll accomplish more physically in 45 days than most people do in a lifetime!…

2014 Dates

Aug /
See all dates



Group Discounts [?]

Rider Type [?]



Hotel Style [?]



Start | End

Portland, Oregon | Portland, Maine


45 days | 44 nights

Beyond Biking

Hiking, Historical Site Visit, Beach, Spa, Shopping


Make it Private [?]

Go Private!

DAYS 1 - 10

The Pacific Northwest | Astoria, OR to Missoula, MT

Begin your journey in the Pacific Northwest, leaving the Pacific Ocean behind and cycling through dense forests en route to the City of Roses, Portland | Marvel at the breathtaking scenery of the Columbia River Gorge, punctuated with countless waterfalls | Sample some of Washington’s finest vintages in Walla Walla | Follow in the footsteps of two of the world’s greatest explorers, Lewis & Clark | Pace yourself over Lolo Pass on the way to a well-deserved rest day in Missoula

DAYS 11 - 19

The Mountain West | Missoula, MT to Rapid City, SD

Ride through Big Sky Country, dotted with cattle ranches and agricultural fields | Test yourself over Bighorn Pass while searching for wildlife | Visit the Energy Capital of the Nation, Gillette, WY, which produces vast quantities of American coal | Take in the majestic splendor of the Devil’s Tower National Monument | Cycle amongst the spruce and ponderosa pines of Spearfish Canyon through the Black Hills | Visit the sculpted granite faces of Washington, Jefferson, Roosevelt and Lincoln during your second rest day at the Mount Rushmore National Memorial

DAYS 20 - 29

The Midwest | Rapid City, SD to Madison, WI

Pedal through the eroded buttes, pinnacles and spires of South Dakota’s Badlands National Park | Ride across vast North American grasslands as stately cottonwoods line small rivers | Keep a watchful eye out for pronghorn during your rides | Continue through the American Heartland, which is flanked by the Missouri and Mississippi Rivers | Watch the topography change as you cross into the undulating terrain of America’s Dairyland: Wisconsin | Enjoy your third rest day in Trek Travel’s hometown of Madison

DAYS 30 - 35

The Great Lakes Region | Madison, WI to Cleveland, OH

Take a brief reprieve from cycling on the Lake Express Ferry across Lake Michigan | Stroll the downtown sidewalks of Holland, Michigan, known as "The Tulip City" for it's Dutch heritage | Cycle through the Irish Hills with countless lakes and pastoral farms | Explore the Rock and Roll Hall of Fame during your well-earned fourth and final rest day

DAYS 36 - 45

The Northeast | Cleveland, OH to Portland, ME

Share the road with a horse and buggy through rural Amish Country | Take a short ferry across the narrow end of Lake Champlain, once protected by the large 18th century Fort Ticonderoga, built to control the river portage | Sample some of New York’s finest wines as you make your way through the Finger Lakes | Ride through New York’s Adirondacks, Vermont’s Green Mountains and New Hampshire’s White Mountains | Celebrate as you make your way into the Old Port District along Portland Harbor | Reflect over the journey completed and the new-found friendships formed

XC Lite

Have limited amount of time?

Only want to join us for the first 10 days of this journey? Start in Pacific Northwest, leaving the Pacific Ocean behind and cycling through dense forests en route to the City of Roses, Portland | Marvel at the breathtaking scenery of the Columbia River Gorge, punctuated with countless waterfalls | Sample some of Washington’s finest vintages in Walla Walla | Follow in the footsteps of two of the world’s greatest explorers, Lewis & Clark | Pace yourself over Lolo Pass on the way to finish with a well-deserved rest day in Missoula CALL FOR DETAILS AND AVAILABILITY


Dates & Pricing


24th / 45 days / 44 nights
$16999 / Person, $3500 / Single OCC.
Sold Out
24th / 10 days / 9 nights
$4199 / Person, $3500 / Single OCC. / XC Lite | Portland to Missoula, call for details
Sold Out

First, Last, and Rest day hotels are listed below, download the PDF itinerary for the full list.

Canary Pier Hotel on our Cross Country bike tour

Cannery Pier Hotel

Astoria, Oregon

Built on the site of the former Union Fish Cannery, the Cannery Pier Hotel is located 600 feet into the Columbia River. From this unique and enviable position, it offers guests unparalleled views of a real working river, as well as views out to Cape Disappointment Lighthouse and the impressive Astoria–Megler Bridge. Each room has a private balcony and a fireplace, hardwood floors, and luxurious amenities. Take advantage of the authentic Finnish sauna before embarking upon the first ride of your long journey.
Hilton Doubletree Missoula on our Cross Country bike tour

DoubleTree Hotel Missoula - Edgewater

Missoula, Montana

The Doubletree Edgewater is located in the heart of the college town of Missoula, on the banks of the Clark Fork River. The campus of the University of Montana is only three blocks away and the restaurants and main attractions of downtown are within walking distance. You may decide to take advantage of the world-class fly fishing right out the door, or maybe just kick back and take in the stunning views of Mount Sentinel and watch the river flow past.
Hotel Alex Johnson on our cross country bike tour

Hotel Alex Johnson

Rapid City, South Dakota

Take some time out on your rest day in Rapid City to delve into the rich history of this hotel, which is registered with the Historic Hotels of America. Hotel Alex Johnson was built in 1928 and has hosted guests including six U.S. presidents. Check out the original Native American art, a display of railroad artifacts and photographs of the celebrities, movie stars, politicians and Presidents who have made the Alex their “home away from home." The hotel recently underwent a multimillion-dollar renovation, including the opening of a new rooftop Art Deco style bar called Vertex. Restoration of the hotel based on original photographs and plans has returned the hotel’s ambiance to that of the 1920s, from the guest rooms to the ballroom to the restaurant and lobby.
Hilton Madison Monona Terrace on our cross country bike tour

Hilton Madison Monona Terrace

Madison, Wisconsin

The Hilton Madison Monona Terrace is perched on the shores of beautiful Lake Monona in the heart of downtown. This bustling, walkable city is the home of Trek Travel, the Wisconsin State Capitol, the University of Wisconsin–Madison Campus, and countless shops and restaurants. Go for a walk on the lakeside bike and walking path, take a tour of the Capitol building, shop on State Street, visit the Madison Museum of Contemporary Art, catch a show at The Orpheum Theater or just grab a beer at The Great Dane, one of our favorites.
Hilton Doubletree Cleveland on our cross country bike tour

DoubleTree Cleveland Downtown - Lakeside

Cleveland, Ohio

Kick back on the shores of Lake Erie at the closest hotel to the Rock and Roll Hall of Fame and Museum. The DoubleTree in downtown Cleveland features an indoor pool and a business center if you want to stay in and rest. If you want to venture out, grab the scheduled complimentary shuttle to all of downtown Cleveland's well-known attractions such as Progressive Field, Quicken Loans Arena, CSU's Wolstein Center, Playhouse Square, and the Warehouse District.
Cross Country USA bike tour hotel

Portland Harbor Hotel

Portland, Maine

The Portland Harbor Hotel is located in the beautifully restored Victorian District of the Old Port and just one block from Portland's vibrant waterfront. Featuring cobblestone streets, galleries, shops, day-spas and many historic landmarks, it's a wonderful place to stroll. Check out the full service marinas on both sides of the harbor during your stay and soak in the sights of this working waterfront. This hotel is Portland's only AAA Four Diamond Property and has earned this recognition for the past 10 consecutive years. The grand beds and feather pillows at this luxury retreat are the perfect place to land at the end of your long ride.

What's Included in the Trip Price?

What's not Included?

What is the weather going to be like?

What are the daily rides like?

What are the options for a non-rider travel companion?

How do I train for my trip?

General FAQs

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Our Guides

Besides our many options in travel styles, dates, prices and destinations, we also accommodate your vacation style each day of your trip. You decide how to spend your time whether it is with the group or exploring on your own, riding a little, a lot, or not at all.

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the full-carbon, ultra smooth Trek Domane 5.9, to the comfortable Trek 7.6 FX Hybrid–both included in the trip cost, to our numerous upgrade options, you deserve the best ride on your vacation.

Your Day. You decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.


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