Week 1: Pacific Ocean to Washington Wine Country
Miles: 373 miles · Elevation: +18,877’ / -17,951'
After meeting at your host hotel for an orientation meeting and dinner, the group kicks off their epic adventure with a shakedown ride to the Wreck of the Peter Iredale where the traditional "rear tire-dip into the Pacific Ocean" ceremony will be held before you pedal to Astoria soaking in the sweeping views. The next day you roll east along the Columbia River Gorge, spin through Portland, cross the misty Bridge of the Gods, and chase waterfalls through the Gorge. By week’s end, you cycle into Umatilla, sharing high-fives after your first week together.
Week 2: Wine Country to Bike Travel Mecca, Missoula, MT
Miles: 338 miles · Elevation: +16,828’ / -14,560'
After a rest day wandering around Walla Walla, WA's vineyard-lined streets, You press onward into Idaho, hug the Clearwater River, and stop at Lowell, where the Selway and Lochsa rivers converge before the steady grind up Lolo Pass (5,233'), shout encouragement at the switchbacks, and cheer as you crest into Montana. You coast into Missoula, spin through the university town, and enjoy the bike atmosphere of the long-distance cycling mecca of the US. A well deserved rest day is in store for you.
Week 3: Missoula, MT to Yellowstone National Park, WY
Miles: 398 miles · Elevation: +18,209’ / -13,601'
You leave Missoula behind and head south into the Bitterroot Valley. By the week’s end, you visit the Big Hole National Battlefield, ride across plains where history and quiet stillness meet, power through the mosquito captial of the lower-48, the Big Hole Valley, ride along the Madison River and enter Yellowstone National Park, WY for another rest day and exploration of the park including Old Faithful
Week 4: Yellowstone National Park to Devils Tower, WY
Miles: 408 miles · Elevation: +17,487’ / -21,435’
You continue to explore the Nation's 1st National Park (1872). You circle geysers, spot elk and bison, and marvel at steaming pools before rolling out of the park through Cody, steeped in frontier lore. Another strenuous climb in the Bighorn Mountains, Powder River Pass (9,666') is in store before you cycle through Buffalo, WY. You share the road through high basins and push into rolling foothills toward Devils Tower National Monument (home to Close Encounters of a Third Kind), banking another week in the saddle.
Week 5: Black Hills of South Dakota
Miles: 362 miles · Elevation: +15,117’ / -17,300’
You surge eastward from and ride toward Devils Tower, circling the massive monolith before gliding into South Dakota. You explore the scenic sights of Spearfish Canyon, the Mickelson Trail, Mount Rushmore, Crazy Horse Memorial and so much more. You end the week in the Black Hills celebrating the week’s milestones.
Week 6: Badlands, Prairies and Minneapolis
Miles: 307 miles · Elevation: +7,191’ / -8,026’
The group rides through the rest of the Black Hills, out of the hills and onto the open prairie and the Badlands National Park. You chase long horizons across the Plains, rotate pacelines through crosswinds, and parallel the Missouri River eastward. You spin into the outer reaches of Minneapolis, circling lakes and coasting on its extensive trails, pausing to savor city life at midsummer’s height.
Week 7: Minneapolis, MN to Milwaukee, WI
Miles: 456 miles · Elevation: +11,990’ / -11,972’
As the week begins, you finish the ride into Minneapolis proper on an extensive trail system and take a rest day. When you leave, you drop south into Wisconsin, ride through La Crosse onto the La Crosse Rail Trail, and tackle the tunnels of the Elroy–Sparta Trail. You glide into Madison, pass Winsonsin's gleaming capitol, and continue on to Milwaukee, where the lakefront closes another strong week. Together you ferry across Lake Michigan and disembark in Muskegon for shoreline riding of 6 miles as a rest day.
Week 8: Michigan Forests and into Ontario, Canada
Miles: 534 miles · Elevation: +7,871’ / -8,106’
The route carries you across Michigan’s fields and forests on a United States Bike Route (USBRS) and then onto Michigan Bike Route 1, where the group presses eastward into Ontario, Canada where the week ends in Morpeth, Ontario at a Provincial Park.
Week 9: North Shore Lake Erie, Niagara Falls, Erie Canal Trailway
Miles: 382 miles · Elevation: +5,801’ / -5,993’
You spin along Lake Erie’s north shore, pass through quiet towns, take a rest day in Fort Erie, ON and return to the US not far from Buffalo, NY, pausing to marvel at Niagara Falls before continuing onward. You join the Erie Canal Trailway, riding side by side on towpaths, passing old stone locks, and tracing history across New York. You finish the week when you you bid the Erie Canal Trailway goodbye at Palmyra, NY as you continue along the Northern Tier route.
Week 10: Adirondacks, Green and White Mountains
Miles: 379 miles · Elevation: +20,429’ / -20,454’
You are climbing into the Adirondacks, where lakes, forests, and ridgelines challenge and reward the group. The biggest week since leaving the Rocky Mountains. You crest Adirondack passes, descend into the Hudson Valley (a rest day at Ticonderoga, NY), and climb again into Vermont. You spin past covered bridges, maple groves, and white-steepled churches, then regroup for summits before pressing into New Hampshire’s White Mountains. Each mile carries the group closer to the final push.
Week 11: The Final Leg to Portland, ME
Miles: 190 miles · Elevation: +10,798’ / -11,173’
You tackle the legendary Kancamagus Highway (2,855'), climbing in unison and descending fast through sweeping curves. You cross into Maine, trace pine forests and rocky shores, and pause in Brunswick before rolling the last coastal miles into Portland, ME. Together you dip wheels in the Atlantic, raise glasses, and celebrate the triumph of a coast-to-coast journey completed celebrating the 250th birthday and 50 years of long-distance cycling.
Disclaimer: Our itinerary depends on securing commercial cycling permits in several National Parks, National Forests, Provincial Parks and other federal and state jurisdictions; many of which we have secured in the past. Our itinerary may change as a result.
