OutsideMay 10, 2026
I Retraced the 2,170-Mile Oregon Trail. Here Are Its Must-See Stops.
An adventurous road trip along the Oregon National Historic Trail reveals treeless plains, remote mountains, river gorges, national park units, and eye-opening lessons about Indigenous and Western history.
25 things in this story
- Oregon TrailTrail2,170-mile historic route retraced by car and foot
- Homestead National Historical ParkSightcommemorates 1800s homesteading laws encouraging settlement
- Ash Hollow State Historical ParkSightfeatures steep path up Windlass Hill with wagon ruts
- Chimney RockSightnational historic site run by the state
- Scottsbluff National MonumentSightbluff rises 800 feet above a quaint river town
- Flyover BrewingRestauranttasty brewpub in Scottsbluff
- Agate Fossil Beds National MonumentMuseumpaleontological hikes and Lakota artifacts
- Fort Laramie National Historical SiteSightfree admission park with trails, ruins, and buildings
- Ayres Natural Bridge ParkSightstop in foothills for natural bridge
- National Historic Trails Interpretive CenterMuseumtop-notch free museum and BLM visitor center in Casper
- Independence RockSightDuring the middle of the 19th century, it formed a prominent and well-known…
- LanderNeighborhoodoutdoor town with bike rentals and singletrack
- Bike MillPlaceoffers rentals and info about singletrack and gravel routes
- Johnny Behind the RocksTrailsingletrack trail for mountain biking
- Great Divide MTB RouteTrailgravel sections for cycling
- Lander Cutoff RoadTrailscenic ride along a foothills spur of the OT
- Sinks CanyonSightriver vanishes underground and reappears at the Rise
- The RiseSightwhere Middle Popo Agie River reappears underground
- Popo Agie FallsSightgradual 1.5-mile trail leads to falls
- Worthen Meadow ReservoirSighttrailhead for backpacking into the alpine
- Stough Creek LakesTrailalpine lakes for overnight backpacking
- Continental Divide TrailTraillong-distance trail in the western Winds
- Fossil HillSightdrive switchbacks to Worthen Meadow Reservoir trailhead
- Devil’s GateSight
- Split RockSight