Search for a place to ride your bike in Oregon

Search by

Enter a Location

Examples: Portland or 555 State St. Salem 55025


The 7 regions of Oregon

Ride Options

Select a Ride Type

Off-road, often dirt

Paved roads or paths

Gravel roads or paths

Our best roads, by bike

Select a Ride Length (in miles)


  • Length:
    10 miles
  • Difficulty:
  • Nearby Cities:
    Bend, Redmond, Sisters
  • Region:
    Central Oregon

Trailhead Elevation: 3883 ft


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.

After leaving the trailhead you begin a meandering climb for a little longer than two miles. You know you’ve reached the top when you get to the wooden bench and the kiosk with information about the Whoops Trail. This is a downhill-only section of trail that is also just over two miles to the bottom. This is a progressive trail, heavily manipulated by the hands of dedicated builders. Jumps, berms, rollers, table tops and hips, all the way down the hill. When you reach the Forest Service road and see signs for Ben’s Trail, I prefer to head right, up the road for approximately 1/4 mile until reaching a left-hand turn onto Jim’s Trail. From here you begin working your way down again. Jim’s becomes Phil’s Trail, and anyone familiar with the riding in Bend has heard of or ridden Phil’s; not that it’s the most challenging or technical trail, but it’s a local/regional legend, the first trail to really bring mountain biking to the area. More descending as you work your way back to the Phil’s trailhead. From here you can begin to climb back out toward Skyliner via Ben’s Trail or Kent’s Trail.

Seasons: Spring – Fall


  1. excellent route!

Share this Trail