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Clarkston to Enterprise

  • Length:
    86.5 miles
  • Difficulty:
  • Best Season(s):
    Spring to Fall
  • Nearby Cities:
    Imnaha, Lostine, Wallowa
  • Region:
    Eastern Oregon
  • Attributes:
    Extended Climbs, Rural

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In Oregon, a bicycle is legally considered a vehicle, and the same Oregon road laws apply. Please “be seen” and practice safe riding. Vehicle traffic, farm equipment and narrow shoulders exist on many Oregon roads, and you may find that construction projects, traffic or other events may cause road conditions or signage to differ from the map results, ride descriptions and directions. For travel options plus weather and road conditions, visit, call 511 (in Oregon only), 800.977.6368 or 503.588.2941. Routes listed on this website are for informational purposes and intended as a reference guide only.

Climb up through high-altitude wheat farms to the tiny town of Anatone (mile 28, population 45) for lunch. From there, the climb continues a few more miles into cool evergreen trees before starting down the thrilling descent of the switchbacks on Rattlesnake Grade. The terrain along the grade transitions to arid scrub and wide-open vistas before you reach the bottom of the descent. As you cross the Grande Ronde it’s hard not to give into temptation to stop for milkshakes at Boggan’s Oasis (mile 38.6). These divine confections provide enough fuel for the remaining 3,500 feet of climbing and 40 miles to Enterprise. At mile 43, as you climb back out from the Grande Ronde to pine meadows with elk and deer, the ride crosses into Oregon.

At mile 66 the ride reaches its highest point of the day, topping out at a little over 4,800 feet. In the distance you can see the snow-capped peaks of the Wallowas rising above Enterprise. With the destination in sight, there is ample motivation to finish strong and enjoy a cold, celebratory beer from Terminal Gravity Brewing and a hot shower at the Arrowhead Ranch Cabins.


  1. […] 1: Clarkston, WA to Enterprise, OR View route Critical numbers: 86 miles and over 7,500 feet of climbing Moment you’ll remember forever: […]

Submitted by

Scott Warren

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