The Gunsight Ridge Loop provides a little bit of everything for the experienced rider, and it should be considered a must-do for the area. The ride starts with a moderate climb up Highway 35 that is followed by a section of forest road. The ride joins the Gunsight Trail for a challenging ridge traverse with fantastic views along the way. Finally, you'll enjoy an incredible descent down the steep Gumjuwac Saddle Trail that leads you back to your car.
The majority of the overall elevation gain occurs with a relatively easy spin up Highway 35. Wide shoulders, sparse traffic, and the mountain air and views make this relatively pleasant for a highway ride. After about a 4.4-mile, 1000-foot climb, cross the highway and cut across the shoulder to the parking area just before the overpass for the Bennett Pass Sno-Park. From the Sno-Park, continue onto Bennet Pass Road, NF-3550, which climbs along a ridge that eventually connects to Gunsight Ridge. The dirt road is a fairly well-maintained and has a few fun descents, some great views, and a few rocky and steep climbs that culminate in a long, steep grind. Be sure to keep a map with you to keep your route straight among the several road junctions. After approximately 4 more miles, Gunsight Ridge Trail #685 leaves on the left with a steep climb up the ridge.
Trail #685 is a challenging singletrack ridge trail with many short, steep climbs, and quick descents. NF-3550 continues just parallel to the trail providing a good bailout option. After a longer descent the trail flattens out, and an obvious side trail to the left leads to a rocky viewpoint of Mount Hood, Mount Adams, and Mount Rainier. This is a good break spot, with most of the distance and climbing behind you. From this point, the trees thin out and the trail adds a few more tough climbs and some technical descents that are punctuated with a series of expansive viewpoints. Keep your eyes open for an obvious side trail to the right leading to a clearing with a view to the southern Cascades. The trail crosses several wildflower meadows before dropping back into the woods as it winds down to the Gumjuwac Saddle Trail junction.
At a four-way junction, keep to the north side of the road to join the Gumjuwac Saddle Trail as it drops rapidly back to the parking area. This is a fairly obvious junction, but it helps to have a map handy. Watch out for hikers and stay under control, as this trail will inspire speed but will constantly challenge riders with tight switchbacks and sudden rock hazards - all of which is flanked by a steep drop-off for nearly the entire descent. That said, this promises to be one of the best descents in the area, with smooth, tight, fast singletrack that demands just enough technical attention to keep riders totally focused all the way back to the highway.