OutsideSep 11, 2026
The Best Trail Towns in the U.S.
Some towns are built for trail lovers. Here are five of the best, from Oregon to Michigan, where great trails and vibrant outdoor communities are right outside your door.
25 things in this story
- FlatironsPlace of worshipBoulder, United StatesSignature landmark slanted sandstone peaks.
- Bear Canyon TrailTrailBoulder, United StatesMan runs through tall grass on trail.
- Deschutes National ForestSightBend, United StatesIt was established in 1908, with border changes following in 1911 and 1915.
- Mount BachelorSightBend, United StatesGo ziplining through the treetops.
- Deschutes River TrailTrailBend, United States12 miles long with mixed surfaces along the river.
- Old Mill DistrictNeighborhoodBend, United StatesGreat place to start your run along the river.
- Max King Trail Running CampPlaceBend, United StatesFounder Max King is a World Mountain Running Champion.
- Tumalo FallsSightBend, United StatesPlunges 97 feet over a basalt ledge into a canyon.
- Pilot ButteSightBend, United StatesExtinct cinder cone volcano within city limits.
- Central Oregon Running KlubPlaceBend, United StatesWeekly runs from town for a three-to five-mile jaunt.
- Foot ZonePlaceBend, United StatesEpicenter of the running community, offers training programs.
- Bend Classic MileFestivalBend, United StatesA race offered by Foot Zone.
- Thump CoffeeCaféBend, United StatesLocal favorite coffee roaster with four locations.
- Bend MarathonFestivalBend, United StatesCome find out what makes Bend so special with a running tour of the best it has to offer.
- YoliRestaurantBoulder, United StatesChef Joe Kim earned three James Beard nominations.
- Deschutes BreweryRestaurantBend, United StatesFounded in 1988 as a brew pub, it is known for such products as Black Butte Porter and Mirror Pond Pale Ale.
- UPP LiquidsRestaurantBend, United StatesRESTAURANT HOURS Sunday through Thursday 11:30 AM – 8:00 PM Friday & Saturday 11:30 AM – 9:00 PM Welcome to UPP…
- Terranaut BeerRestaurantBend, United StatesNew Brewery in Bend, Oregon.
- Open Space and Mountain ParksSightBoulder, United StatesManages 46,000 acres of protected land.
- Deschutes RiverTrailBend, United States
- North ForkTrailBend, United States
- Bridge CreekTrailBend, United States
- South ForkTrailBend, United States
- Swede RidgeTrailBend, United States
- 10 Barrel Brewing Co.RestaurantBend, United States