Ride the Modern Oregon Trail - Oregon Trail Rides

Jun 18, 2024

The Oregon Trail is a legendary route that 19th-century settlers once traveled. Starting in Independence, Missouri, and ending in Willamette Valley, Oregon, this adventure will allow you to experience America's small-town charm, snow-capped beauty, and rich historical treasures.

The roadside scenery is stunning, with the Oregon Trail running past some of America’s top landmarks and national parks. You'll feel the excitement riding towards Mt. Hood and Timberline Lodge. In Wyoming, you'll be surrounded by Yellowstone, the United States’ oldest national park. A detour into South Dakota offers a chance to marvel at the massive granite monuments of Mt. Rushmore and Crazy Horse.

In this blog, we’ill provide a few different motorcycle routes in the states that the modern Oregon Trail passes through. Whether you're looking for a motorcycle in Oregon or interested in exploring Oregon Trail rides, these routes, all conveniently connected via US 20, will guide you through an unforgettable journey.

NOTE: These motorcycle routes are primarily for experienced riders ready to ride for days at a time. Breaks are highly recommended–not only to enjoy the area around you, but to prioritize rest. These can be lengthy rides, so please ride with caution!

Route 1: Ride to Menno-Hof Mennonite-Amish Visitor Center — Shipshewana, Indiana

The Menno-Hof Mennonite-Amish Visitor Center in Shipshewana, Indiana, is approximately 600 miles away from the start of the Oregon Trail and can be used as an alternative starting point for those who want a full-length experience of the trail. This route offers a unique detour for those interested in the Oregon Trail, showcasing the rich Amish and Mennonite heritage.

In Indiana’s Amish country, the main attraction is the Menno-Hof Mennonite-Amish Visitor Center, built by locals during a six-day barn-raising. This educational center features exhibits on Amish life, including a mock “sailing boat” and “torture chamber.”

Nearby, Middlebury offers the Pumpkinvine Nature Trail, a converted railroad line. Shipshewana and Middlebury are connected by County Road 16. From US-20, head south on IN-5 into Shipshewana or south on IN-13 into Middlebury.

Hungry travelers should try Das Dutchman Essenhaus in Middlebury, a popular Amish-style buffet, or the Village Inn on Main Street for coffee and pie. The Menno-Hof Center is open Monday through Saturday with a $7 entrance fee.

This route is a perfect example of the diverse experiences on motorcycle rides in Indiana, tracing the footsteps of Oregon Trail pioneers.

Route 2: Visit Mt. Rushmore — Keystone, South Dakota

From the Menno-Hof Mennonite-Amish Visitor Center in Indiana, continue your journey on US-20, which runs across Wyoming and Nebraska. A short detour using US-385 takes you to Mt. Rushmore Memorial Park, an iconic landmark that can't be missed on your Oregon Trail adventure.

Mt. Rushmore, located on the eastern side of the Black Hills, features the colossal heads of Presidents Washington, Jefferson, Lincoln, and Roosevelt. Sculptor Gutzon Borglum designed this monument, which was constructed from 1927 to 1941. Each president was chosen to represent the birth, growth, development, and preservation of America.

While you’re here, make sure to visit the Crazy Horse Memorial, a 563-foot monument still under construction but already the world's largest mountain carving. This massive sculpture is just a short ride from Mt. Rushmore and offers a breathtaking sight.

To reach Mt. Rushmore from US-20, take US-18 at Lusk, Wyoming, then head north on US-18 East into South Dakota. Turn left onto SD-89 North, which becomes US-385. Follow the signs to Mt. Rushmore via SD-244 East. 

The detour adds a great experience to your journey, even if it’s not the closest to the Oregon Trail's path. Taking a well-deserved day-long break to enjoy this area will be worth it after such a lengthy ride! The next few routes will bring you back in line with the Oregon Trail, giving you the full historical and scenic experience of this legendary path.

Want a Local to Show You Part of the Trail?

A trip along the modern Oregon Trail covers thousands of miles across some of the most dramatic landscapes in the country. Riders Share offers guided motorcycle tours across the country, led by locals who know the roads through places like Yellowstone and the Cascades. If you'd rather have a guide for one leg of the journey while tackling the rest on your own, a guided tour is a great way to add depth to a route this size.

Route 3: Explore Yellowstone National Park — West Yellowstone, Wyoming

From Mt. Rushmore in South Dakota, continue your ride to Yellowstone National Park, located in the northwest corner of Wyoming and extending into Montana and Idaho. Although not directly on the Oregon Trail, Yellowstone is in one of the states the trail passes through, making it a must-see detour for any rider.

Yellowstone is a sightseer’s dream, offering geysers, waterfalls, canyons, rivers, mountains, and massive herds of buffalo. Old Faithful Geyser is a highlight, with its regular eruptions perfect for a postcard-worthy picture. The Old Faithful Basin area also includes the Old Faithful Visitor Education Center and the highest concentration of geysers in the world.

Yellowstone’s Grand Canyon, with its massive waterfall, is another must-see. Several trails let you hike around the canyon's edge, showing off the natural beauty of the park's 2.2 million acres. You could spend a week exploring Yellowstone's wide-open spaces.

The park has many hotels and lodges offering cafeteria-style dining, along with plenty of gas stations, gift shops, and general stores. There’s a $30 entrance fee, but you can pair it with a pass for Grand Teton National Park nearby for a total of $50.

For those tracing the Oregon Trail, this route offers a chance to experience one of America’s most stunning national parks. Yellowstone motorcycle rides provide a mix of natural wonders and the adventurous spirit that the Oregon Trail is known for.

Route 4: Timberline Lodge — Government Camp, Oregon

From Yellowstone National Park, head west to Timberline Lodge in Government Camp, Oregon. This route takes you through the stunning landscapes of Idaho and into Oregon, closely following the path of the original Oregon Trail.

Timberline Lodge, east of Government Camp, was built in the 1930s by local workers under the direction of Franklin D. Roosevelt’s Works Progress Administration. Now a national historic landmark, it stands as an example of Depression-era architecture.

When you arrive, you can explore the lodge's impressive features, including a huge fireplace, a three-story main lobby, and verandas with views of the Cascade Mountains. Even if you're not staying at the lodge, it’s worth visiting for its historical value and architectural beauty.

For those interested in activities other than motorcycling, the nearby ski resort is open year-round and has one of the longest skiing seasons in the United States. Step off your motorcycle rental and onto some skis to enjoy the powdery slopes.

This route is perfect for motorcycle riders interested in the Oregon Trail, offering a mix of historical landmarks and recreational activities. Timberline Lodge provides a unique stop that adds to the journey along the trail's historic path.

Experience these Routes Along the Modern Oregon Trail with a Motorcycle Rental from Riders Share

Ready to explore the modern Oregon Trail? Riders Share has the perfect motorcycle rentals for every need, whether you're tackling tough mountain roads, scenic highways, or off-road trails. With a wide selection of motorcycles to choose from, you'll find the ideal ride for any route and all terrains. Start your adventure today with a motorcycle rental from Riders Share and experience the journey of a lifetime.

Last Stop

As you finish your journey along the modern Oregon Trail, you'll have experienced some of the most iconic and breathtaking routes in the country. From the rich cultural heritage in Indiana to the monumental sights of South Dakota, the natural wonders of Wyoming, and the historic charm of Oregon, each stop offers a unique glimpse into America's diverse landscape. So, gear up and start planning your adventure with Riders Share. The open road is calling, and the Oregon Trail awaits!