Sometimes you want to climb, and other times you want to glide. When it’s the latter you’re after, grab a shuttle from Cog Wild to Dutchman Flat Trailhead, 20 minutes west of Bend, for this mostly downhill ride that’ll take you right back to town, where an IPA awaits.
Starting from Dutchman Flat, you’ll climb just a bit to the ride’s high point of 6,500 feet—then get ready for a fun, adrenaline-filled descent. The singletrack drops fast and smooth, with bermed turns to give you that grin-producing swoop effect.
You’ll briefly climb again to the end of the Swampy/Dutchman Trail where it intersects with the Ridge Loop Trail, but pretty soon it’s back to gliding downhill. Just make sure you pay attention as you come to a number of other intersections—it’s a good idea to have your phone with you to help with navigation.
At about mile 7.5, hop onto the South Fork Trail and get ready for some even more serious fun. You’ll pick up speed and fly through the kind of wide-open sections you dream about in the off-season. Then there’s an easy climb up through vanilla-scented ponderosa pines on Skyliners Trail, followed by yet another thrill: two miles on the aptly named Lower Whoops Trail. Ride the tables and savor the huge berms; it’s a descent-only trail, so go for it with all you’ve got. And go back up Forest Road FS-310 if you want to ride it all over again (you will).
After Lower Whoops, you have seven miles to go, all on singletrack. The ride ends with yet more elevation drop on Phil’s Trail, ending at Phil’s Trailhead. Catch your ride there, or better yet, ride a few minutes on the bike path alongside Skyliners Road to reach downtown Bend. That IPA is waiting for you at Brother Jon’s Public House .
Riding Season
The ride starts near Mt. Bachelor, so expect snow until early summer. There are lower access points you can reach earlier in spring, but really the best time to savor the whole ride is fall.
