Southwest of Bend in the Deschutes National Forest, the Round Mountain/Lookout Mountain Route is a 23 mile double track providing a same-day challenge of two mountain peaks for the motivated mountain bike rider. Drive 16 miles south of Bend on Hwy 97 and take the Fall River/Hwy 42 exit. Head 20 miles west on Hwy 42 to the Crane Prairie Campground turnoff and make a right turn onto FS 4270. Drive 4.5 miles down FS 4270 to the Crane Prairie Campground/Resort and park in the day use area. Head out of the Campground and turn left onto FS 4270, then make a right onto the gated road FS 255. Follow FS 255 till it goes through another gate and joins FS 250. Bear right onto FS 250 and follow this double track till it joins the red cinder road FS 200. Bear left onto FS 200 and continue on to the junction with FS 4253. At this junction head straight onto FS 4256 and make the arduous 2.5 mile climb up to the top of Round mountain. The views from the top of Round mountain at the fire lookout are exceptional. To continue, return the way you came on FS 4256. At the bottom turn left and follow FS 4253 the short distance out to FS 4250 and turn right. After a short distance you will turn left onto FS 300 and then right onto FS 500. Ride up FS 500 for approximately 2.5 miles till you reach FS 4245 where you will make a left. Ride for about 0.5 mile up FS 4245 to the junction of FS 700. Here you can choose to continue up FS 4245 and make the optional 2.5 mile climb to the top of Lookout Mountain or continue along FS 700. Continue heading straight along FS 700 as it becomes FS 950 and then FS 960. Finally you will come to FS 600 where you will turn left and follow this down for 2.0 miles to FS 4250. Make a right onto FS 4250 and mountain bike ride down to FS 4270 and turn left. Follow FS 4270 the 1.5 miles back to the trailhead.
Overall, Round Mountain/Lookout Mountain Route is the 19th most popular mountain bike trail of all 55 mountain biking rides in Oregon.