Road trips are a great opportunity to connect with your travel companion (besides listening to a killer playlist or gripping podcast series, it’s basically just tons of time for long convos), sightsee beautiful scenery and stop at some pretty cool places along the way. You’ve already done Route 66 and soaked in the coastal splendor of Highway 1, maybe even looped around the Road to Hana, but what about the Oregon Trail? Yes, the real-life route that more than 400,000 pioneers traveled from 1840 to 1880 and later inspired the classic computer game every ‘90s kid played. Following the 2,170-mile Pathway to the West that connects Independence, Missouri to Oregon City, Oregon, the Oregon Trail is one of the most interesting American road trips, full of history and fascinating pit stops, plus you can also spend the night in some great more modern destinations (because who doesn’t enjoy a little art, culture and cuisine between peeping preserved wagon ruts?)—and we’ve mapped it out. So all you have to do is fill your tank, buckle up and drive.
The Ultimate Oregon Trail Road Trip Itinerary
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- Getting There: 20 minutes from Charles B. Wheeler Downtown Airport
- Where to Stay: Large Historic Remodeled Home, Modern Home in Woods, Woodstock Bed & Breakfast
Yes, Independence is the literal starting point of the Oregon Trail and for that, it’s the place the route—and your road trip—will inevitably kick-off, however, this Missouri city deserves more credit than just a historically significant dot on a map. It’s perhaps best known for the Truman Library & Museum, which has a permanent collection of information and relics about the Independence-born president. While the popular Frontier Trails Museum showcases pioneer-era relics and does wagon tours. Oh, and you’ll definitely want to chow down on some homemade American comfort food before hitting the road.
PITSTOP: Oregon Trail Nature Park (St. Mary's, Kansas)
- Getting There: 2 hours 50 minutes from Independence, MO
- Where to Stay: Maryann’s Guest House
It would be easy to overlook Blue Rapids, located approximately 12 miles south of Marysville, but then you’d be missing out on the chance to witness Alcove Springs. A popular stop for weary travelers after crossing the Big Blue River, it boasts unique rock formations—many of which still showcase names carved centuries ago—a waterfall and, as the name would suggest, natural springs. Another claim to fame that’s not Oregon Trail-related though still interesting is that Blue Rapids holds the title of the smallest town in the United States to have hosted a national league baseball game.
PITSTOP: Rock Creek Station State Historical Park (Fairbury, Nebraska)
- Getting There: 5 hours 15 minutes from Blue Rapids, KS
- Where to Stay: Ogallala Family Home, Holiday Inn Express & Suites
Ogallala is a cool little city in Keith County with a population of 4,700 residents that you might recognize as a stop on the Pony Express and the transcontinental railroad. Consider spending the night in Ogallala, so you can wake up with fresh legs to hike California Hill just outside of nearby Brule. It was a particularly treacherous and essential part of the Oregon Trail journey. You can still see the deep ruts from wagon wheels even today. The panoramic views are pretty epic, too. Plus it’s a good excuse to get the blood flowing after all those hours in the car.
A tiny town that’s big on historic and natural beauty, Guernsey showcases tons of Oregon Trail remnants. First up, head about three miles outside of town to Oregon Trail Ruts State Historic Site to see some of the best-preserved wagon marks anywhere. We’re never one to pass up an opportunity for some scenic hiking, especially after a lot of driving. Guernsey State Park is the perfect spot to stretch your legs and soak in the views of sandstone cliffs. If you’re keen on more outdoor recreation before getting back in the car, there’s boating, biking and fishing (it’s Wyoming, after all).
PITSTOP: Independence Rock (Casper, Wyoming)
- Getting There: 6 hours 45 minutes from Guernsey, WY
- Where to Stay: Grandma’s House, Paris House, Country Cottage
Chances are Sun Valley and Sandpoint are higher up on your Idaho travel list than Montpelier but fans of Oregon Trail lore know about Big Hill, a fabled challenge that ranked as the longest, steepest climb on the entire route. And the descent was even more difficult. Needless to say, Big Hill is a big deal. Another old-timey attraction worth checking out? The Bank of Montpelier, which was established in 1891, was robbed by Butch Cassidy and his Wild Bunch Gang in August 1896. It’s the only financial institution the infamous outlaws hit that’s still standing.
PITSTOP: Fort Hall Replica (Pocatello, Idaho)
6. Boise, Idaho
- Getting There: 4 hours 45 minutes from Montpelier, ID
- Where to Stay: Newly Renovated Bungalow, Modern Farmhouse, Home2 Suites by Hilton
Boise is a lively city that will provide a fun change of pace in contrast to some of the smaller towns on your route thus far. The capital of Idaho has many exciting attractions such as the Boise Art Museum, where contemporary works adorn the walls of an Art Deco building and outdoor sculptures make their presence known in the garden. The Boise River Greenbelt, a series of trails and parks along the water, is another huge selling point and a lovely way to spend the afternoon. To up the ante on outdoor adventure, visit Boise National Forest.
PITSTOP: Philip Foster Farm National Historic Site On The Barlow Road/Oregon Trail (Eagle Creek, Oregon)
- Getting There: 6 hours 45 minutes from Boise, ID
- Where to Stay: Stonehouse, Floating Bungalow, Happy Rock Inn
The official end to the Oregon Trail, Oregon City obviously deserves a visit for historical purposes but it’s also a great place with many modern charms, too. On the heritage side of things, costumed guides take visitors through interactive exhibits that better reveal what life was like in the mid-1800s at the End of the Oregon Trail Interpretive Center. Don’t miss the Museum of the Oregon Territory either. Oregon City is also home to one of the great American Main Streets. A walk along this revitalized thoroughfare reveals why. It’s lined with an enticing array of shops, cafes, restaurants and breweries.
PITSTOP: Willamette Falls (West Linn, Oregon)
- Getting There: 50 minutes from Oregon City, OR
- Where to Stay: Atticus Hotel, Downtown Cottage, Half-Pint Farmhouse
Many settlers continued past Oregon City to Willamette Valley—and you should, too. Sure, it’s a region rather than a singular stop, however, it’d be pretty incomplete for us to spotlight a cute place like McMinnville without mentioning Carlton, just a few minutes down the road. Surrounding the quaint towns are sprawling vineyards that grow some of the best Pinot noir in the country. It’s pretty fortuitous that Willamette Valley caps off the trip because you’re not going to be driving anywhere after wine tasting.