The Ultimate Oregon Trail Road Trip Itinerary

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.
1. INDEPENDENCE, MISSOURI
- Getting There: 20 minutes from Charles B. Wheeler Downtown Airport
- Where to Stay: Large Historic Remodeled Home, Modern Home in Woods, Woodstock Bed & Breakfast
PITSTOP: Oregon Trail Nature Park (St. Mary's, Kansas)
2. BLUE RAPIDS, KANSAS
- Getting There: 2 hours 50 minutes from Independence, MO
- Where to Stay: Maryann’s Guest House
PITSTOP: Rock Creek Station State Historical Park (Fairbury, Nebraska)
3. OGALLALA, NEBRASKA
- Getting There: 5 hours 15 minutes from Blue Rapids, KS
- Where to Stay: Ogallala Family Home, Holiday Inn Express & Suites
4. GUERNSEY, WYOMING
- Getting There: 3 hours 12 minutes from Ogallala, NE
- Where to Stay: Camper, Bunkhouse Motel
PITSTOP: Independence Rock (Casper, Wyoming)
5. MONTPELIER, IDAHO
- Getting There: 6 hours 45 minutes from Guernsey, WY
- Where to Stay: Grandma’s House, Paris House, Country Cottage
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
PITSTOP: Philip Foster Farm National Historic Site On The Barlow Road/Oregon Trail (Eagle Creek, Oregon)
7. OREGON CITY, OREGON
- Getting There: 6 hours 45 minutes from Boise, ID
- Where to Stay: Stonehouse, Floating Bungalow, Happy Rock Inn
PITSTOP: Willamette Falls (West Linn, Oregon)
8. WILLAMETTE VALLEY, OREGON
- Getting There: 50 minutes from Oregon City, OR
- Where to Stay: Atticus Hotel, Downtown Cottage, Half-Pint Farmhouse
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