Motorcycle Riding on the Modern Oregon Trail

Nov 6, 2021


Motorcycle rental ridden during a Riders Share motorcycle rental trip.

If any modern route deserves to be named after the Oregon Trail, US-20 highway is it. Running between Portland, Oregon and Boston, Massuchusets US-20 is the modern version of the difficult journey 19th-century settlers made between Missouri to Oregon. During this adventure you’ll sample every aspect of America, from its humble small-town charm, to its snow-capped beauty. US-20 is an education in the nation’s natural and historical treasures.

The roadside scenery is gorgeous, but the Oregon Trail has the good fortune of running past America’s top landmarks and national parks. You’ll likely get a shiver up your spine as you ride up toward Mt. Hood and Timberline Lodge, featured in Stanley Kubrick’s 1980 horror flick, The Shining. Journey into Wyoming and you’ll be surrounded by Yellowstone, the United State’s oldest national park. Take a detour into South Dakota, and lose yourself among the massive granite monuments of Mt. Rushmore and Crazy Horse.

Save yourself the trouble and book a motorcycle with Riders Share. It makes finding a ride in Portland or Boston the easiest part of the journey.

1. Timberline Lodge — Government Camp, Oregon

Stanley Kubrick fans riding the Oregon Trail are in for a treat. Timberline Lodge, seen prominently in the 1980 horror classic The Shining, lies east of Government Camp, Oregon, not far from the junction of US-26 and Highway 35. Timberline Lodge was built in the 1930s by local artisans under direction of Franklin D. Roosevelt’s Works Progress Administration. It’s now a National Historic Landmark and an example of Depression-era architecture. 

Even if you’re not staying at one of this family-owned lodge’s sumptuous hotel rooms, pay a visit to its colossal fireplace, three-story main lobby, and stunning verandas looking out onto the Cascade Mountains. Don’t feel pressured sticking with one mode of transportation while you’re there—exchange your motorcycle rental for some skis and hit the powdery slopes nearby. The ski resort is open all-year-round and boasts one of the longest skiing seasons in the United States. 

Timberline Lodge sits on the south side of Mount Hood, 60 miles from Portland. Hungry? Dine at the Cascade Dining Room, Blue Ox, or Ram’s Head Bar for award-winning food. 

2. Yellowstone National Park — West Yellowstone, Wyoming

As you ride through Oregon, Idaho, and Wyoming, you’ll have the opportunity to see the world’s oldest national park. Nestled in the northwest corner of Wyoming and extending into portions of Montana and Idaho, Yellowstone National Park is a sightseer’s dream.

Geysers, waterfalls, canyons, rivers, mountains, and massive herds of buffalo await the rider willing to explore. Old Faithful Geyser is so well-known that you’ll have to take the time to snap a postcard-worthy picture during one of its frequent eruptions. The Old Faithful basin area is home to the Old Faithful Visitor Education Center and the highest concentration of geysers in the world.

Yellowstone’s Grand Canyon—not to be confused with its more famous cousin in Arizona—is home to a massive waterfall. You can hike around the edge of the canyon using several trails. This untouched spread of natural beauty covers 2.2 million acres of unfarmed land, so you could spend a week exploring Yellowstone.

You can get grub at any of the park’s hotels and lodges, usually from cafeteria-style restaurants. Gas, gift shops, and general stores are plentiful throughout. There’s a $30 entrance fee, but if you want, you can pair it with a pass for Grand Teton National Park nearby for a total of $50. 

3. Mt. Rushmore — Keystone, South Dakota

US-20 runs across Wyoming and Nebraska, but a short detour using US-385 takes you to America’s granite love letter to its greatest presidents—Mt. Rushmore Memorial Park.

Located on the eastern side of the Black Hills, this constellation of presidential heads is an obligatory stop. Sculptor Gutzon Borglum designed and oversaw the construction of the monument from 1927 to 1941, selecting the four presidents as representations of the birth, growth, development, and preservation of America.

Bring a high-quality camera, get off your bike, and snap a photo with Washington, Jefferson, Lincoln, and Teddy Roosevelt for scrapbook. Since you’ll take the US-385 to Mt. Rushmore, make sure you check out the Crazy Horse Memorial in Crazy Horse, South Dakota. Although each of Mt. Rushmore’s presidential heads stand 60-feet tall; it pales in comparison to Crazy Horse, a 563-foot monument 10-times the size of Mt. Rushmore. This massive sculpture might be a work in progress, but it’s still a breathtaking sight and the world’s largest mountain carving.

Make your Mt. Rushmore detour by getting off of US-20 and onto US-18 at Lusk, Wyoming. Head north on US-18 East until you pass into South Dakota and have an opportunity to turn left onto SD-89 North. Follow SD-89 North until it becomes a part of US-385 past Pringle, South Dakota. Make a right onto Custer Street/Mt. Rushmore Road in Custer, South Dakota, and then make a left onto US-16 East/US-385 North/North 5th Street. Make a right onto Avenue of the Chiefs if you want to get to Crazy Horse; otherwise, stick to the road until you can make a right onto SD-244 East. SD-244 East will take you to Mt. Rushmore. Follow US-386 south past the South Dakotan towns of Hot Springs, Maverick Junction, and Oelrichs to get back onto US-20.

4. Menno-Hof Mennonite-Amish Visitor Center — Shipshewana, Indiana

You might have rented the latest-and-greatest motorcycle in Boston, but get ready to meet older modes of transportation once entering Indiana’s Amish country on US-20. Aside from the beautiful countryside, the main attraction in Amish Country is the Menno-Hof Mennonite-Amish Visitor Center outside the hamlet of Shipshewana. Amish and Mennonite locals built this educational center in a barn during a six-day barn-raising. You’ll learn all about the lives and struggles of the Amish people through high-tech multimedia exhibits, including a mock “sailing boat” and “torture chamber.” Seven miles down the road is another Amish town, Middlebury. Visit the Pumpkinvine Nature Trail for a walk along a railroad line that’s been converted to an arboretum of fruit trees.

Shipshewana and Middlebury are connected by County Road 16. If you’re coming from the east on US-20, make a right onto IN-5 (South Van Buren Street) and ride into Shipshewana. If you’re coming from the west, make a left onto IN-13 (South Main Street) and ride into Middlebury. Hungry travelers should try eating at Das Dutchman Essenhaus—it’s a popular all-you-can-eat buffet, inn, conference center, and shop in Middlebury serving Amish-style food to 750,000 people a year. For a lighter, less-crowded stop, try the Amish-run Village Inn on Main Street. This country cafe serves fantastic coffee and handmade pie. The Menno-Hof Mennonite-Amish Visitor Center is open Monday through Saturday and has a $7 entrance fee.

5. Minute Man National Historical Park — Concord, Massachusetts

Even more tantalizing than Boston, the site of Paul Revere’s Night Ride, is the “shot heard round the world” and the famed homes of Concord, Massachusetts. A lot smaller and more intimate than the big city, Concord boasts the distinction of being the first battle of the American Revolutionary War. The Old North Bridge, where the opening shot of the conflict was fired, stands over the Concord River. Concord is also the site of the homes of famous New England writers Ralph Waldo Emerson, Nathaniel Hawthorne, Henry David Thoreau, and Louisa May Alcott. Emerson’s study in The Old Manse is particularly well-preserved and a window into the everyday life and experiences of one of America’s greatest essayists. Visit Walden Pond near dusk to get a sense of the magic Thoreau conveyed in his famous work of the same name, or pay your respects at Hawthorne’s home, The Wayside, in the Minute Man National Park. Bring your entire journey to a close by visiting the Concord Museum, home to dozens of personal items belonging to Emerson and Thoreau, as well as the lantern used in Paul Revere’s famous ride!

You’ll ride along the MA-2 if you’re making your way to or from Boston, so getting to Concord is little more than making a small detour. Stick to MA-2 coming out of Boston until you reach Walden Pond. Here, make a right onto Walden Street. Follow Walden Street until you can make a right turn onto Heywood Street. Make an immediate left turn onto Lexington Road. This puts you in the center of town.

Riders looking for longer-term stays in the Portland and Boston areas are encouraged to check out motorcycle routes located nearby (read the Top-5 Motorcycle Routes Around Portland and History-Filled Motorcycle Routes Near Boston articles). Portland’s motorcycle routes are brimming with natural beauty, while Boston’s are better suited to the history enthusiast interested in America’s colonial past.