This is the most classic loop in the Ochoco National Forest and it's located just east of Prineville, OR. This can be split into Round Mt. only (loops or out-n-back), Lookout Mt. (best as a loop) or the whole enchilada. Riding both together in one day can take up to six hours for 30 miles with 5500 of climbing. There are other trails to ride in the Ochocos, but this pair is easy to find, fun for riding, and proves a very rewarding backcountry experience.
The ride starts on pavement for the climb to Walton Lake, then turns to forest road and soon to singletrack up over Round Mt and down to a short section of pavement near the saddle between Round Mt and Look Out Mt, before climbing again on a gravel road to near Independence Mine and singletrack to the summit of Lookout Mt. Big views and alpine wildflowers at the summit, before a steep, technical set of switchbacks down into the forest for a fast, long descent through old growth Ponderosa pine to the old guard station where you started. Includes some very steep sections and potential to run into horses, but few people in general.
The remoteness of the ride and the lack of cell reception means it's a long way out to get help if someone biffs, so ride carefully and give way to the hikers and horses. A pit toilet is available at the old guard station, but that's the last facility you'll have and water isn't generally available along the ride, so bring plenty. It's not advisable to bring a dog, as it can be a hot ride and there's little to no water available. The old Independent Mine has been cleaned up in recent years, but some contamination undoubtedly remains, so don't drink the water in that vicinity as it's likely still toxic.
All options begin at the old Lookout Mountain Guard Station at the base of Lookout Mt. and it's best to ride clockwise. So begin both ride options with a road climb for Round Mountain head left one-half mile above the Guard Station toward Walton Lake, for just Lookout Mt. stay on that road to head to toward Mitchell.
To access the Round Mountain Trail #805, ride up Forest Road 22 (paved) to a gravel service road (on your right) just past and across from the entrance to Walton Lake. Climb this gravel road a short distance to a small parking area and trailhead for the Round Mountain Trail #805, which immediately climbs through a meadow and into the forest where the real climbing begins. Follow the trail up switchbacks through forest and meadow until the trail intersects the gravel radio tower service road, just below the summit of Round Mt. (the summit itself has radio & cellular towers on it not very scenic).
Turn left and descend the service road a short distance to a trail marker on your right (you're now back on Trail #805), then proceed on the trail heading South toward Lookout Mt. The Round Mountain Trail #805 itself intersects Forest Road 42 just east of the saddle between the two mountains. Turn right on Road 42 and climb a very short distance to the saddle. If you've had enough climbing at this point, you can continue on Road 42 and descend the pavement all the way back to the old Guard Station where you started.
Assuming you're still game for more climbing and a great singletrack descent, turn left (south) and climb the gravel road past a large, flat parking area often filled with horse trailers. The gravel road continues to climb toward the south to the upper parking area (on your left) near an abandoned mining village associated with the Independent Mine.
While there are multiple routes to the summit of Lookout Mountain, the preferred route continues east out of this upper parking area on a well shaded singletrack trail before ascending a ridge into open meadows with scenic views, then descends to cross Brush Creek, and then climbs again to reach the summit of Lookout Mt. where the site of an old FS lookout stood. All that is left at this site is a small rock wall.
Several hundred yards below the summit to the Northeast in the trees is a Shelter hut, but the Lookout Mountain Trail
stays on the long ridge line heading generally northwest. In the first mile of this descent, there is some significant exposure and technical, rocky sections. During the long descent, there are three healthy climbs, the last one being the longest. The final stretch back to where you parked is fast and flowy.
Lookout Mt. and the Ochoco Mts have a long history of mining, logging and grazing, but the remaining old-growth Ponderosa pine forests are some of the most interesting and beautiful in Central Oregon. Lookout Mt is a great backcountry ski tour to the hut and summit when the snow conditions are good and particularly if the road into Big Summit Prairie has been plowed (it typically hasn't been).