Gray Butte is very near Smith Rock State Park and is one of the more scenic rides in the area both for the views of Smith Rock and the Cascades in the distance. The riding is relatively strenuous for the most part. It is not too technical except for some loose rocks on the southwest side of the butte on one of the bigger descents. Depending on how you structure the ride a fair amount of the riding may be on dirt roads, on the east side of Gray Butte and the Burma Road near Smith Rock. This area is different than most of the riding in Central Oregon in that it is more arid with juniper trees and when it does rain the trails can get unusually muddy for Central Oregon. Other than the trails in the state park itself these trails get quite a bit of use from horseback riders and cows and can suffer accordingly. The cows are doing a lot of damage and really do not belong in this environment but that is an editorial for a different website.
Most of the
land around the butte is here is part of the Crooked River National Grassland
which is part of the Forest Service not the BLM. Technically the Gray Butte
Trail starts on the north side of Gray Butte and goes around the west side of
the Butte down Sherwood Canyon to the top of the Burma Road near Smith Rock
State Park. This could be done as a shuttle which is normally not advocated on
this site but in this area more traffic will help smooth the hoof prints of
cows and horses. It can also be ridden from Smith Rock going up the Burma Road or the north side of Smith Rock. Burma Road is a lot of work and most people complain about the steep climb. The ride around Smith Rock is easy and scenic until you get to the north side then there are a couple dozen switchbacks up to where it joins the steeper Burma Road. If you are into climbing the north side of Smith Rock up around the west side of Gray Butte is a good one however the scenery is mostly at your back and the descents are not very good for the climbing effort. The hairpin turns on the north side of Smith Rock are so tight they necessitate almost coming to a complete stop from high speeds.
Without doing a shuttle here is a recommended ride. Start from Skull Hollow Campground and ride up the dirt road on the east side of the butte to the north side for the first few miles. This will entail some climbing with little scenery but be patient it gets much better. There is a road heading west about a mile up from the campground. Keep going straight. You will come back down that road on a parallel single track called Cole Trail. The start of the Gray Butte trail is just past an old abandon orchard and has a trail head sign if it is not shot to pieces. You could ride it clockwise but you would then be ascending on single track and descending a loose gravel road.
The Gray Butte single track is not all descending and starts with more climbing followed by some nice rolling terrain with views. Part way around you will come to a gate and an option to head northwest on Cole Loop Trail. Keep going straight on what is now for about a mile both Cole Loop and Gray Butte trail. After descending for quite a while off the south west side of the butte, you will come to a road #5720 in a pass of sorts (the top of Sherwood Canyon - cow pie pass). For the short version look for a trail on the left called Cole Loop and descend back to Skull hollow. For a longer version cross the road and continue south on the pass until the Gray Butte trail veers off to the west toward Smith Rock. Once you are on it, you will be flying down Sherwood Canyon ever so slightly downhill. The trick is to be able to take in the gorgeous scenery while your speeding down the trail that drops off steeply to your right. It is not very technical, but pretty thrilling none the less, and well worth the gradual ride back up. You could continue to Smith Rock if you had a vehicle there. Unfortunately the descent back to Skull Hollow from the pass that used to be great is getting increasingly eroded from damage caused by cattle. Also as mentioned above once you get to the Burma road there are no good descending options that do not involve a lot of heavy breaking. Another option although short that would be very scenic is just to ride back and forth around Smith Rock but this would be best done when there are not a lot of hikers and climbers on the trail.
For all you mountain bikers that also occasionally hit the pavement there are some excellent low traffic paved roads in the area. Doing a mountain bike loop back to Smith Rock that involves some of these paved roads makes for a nice spin.
There are a couple of other trials in the area that are multi use and could be done on a mountain bike but are not real popular at the moment. These are the Cole Loop and Warner Loop Trails. Here is a link to a map put out by the National Forest Service on those trails. These are pretty heavily used by horseback riders but cover some very doable terrain for a mountain bike. Go in a big group and take turns breaking trail or ride last with a dust mask? They also have a map for the Gray Butte Trail. Why they didn't put all these trails on one map is a mystery. After obtaining the trail files from National Forest \ Grassland a map was made with all the trails in one map and it is listed below.
A possible beginner ride would be to start at Skull Hollow and instead of riding the loop counterclockwise go left on road #5720 (the first real road you can make a left on). Pick up the Cole Loop Trail on the right side of the road, go up to the pass and descend Sherwood Canyon to the Burma Road then turn around and come back. This ride would not be too strenuous or technical but would be fun and scenic. You could also ride up the road to make the climb easier but finding the trail to come back down might be a little more difficult. There is a short section on the ride down to Smith Rock where the single track becomes double track and climbs steeply. After this short climb on a road the single track trail resumes its gradual decent the top of Burma Road. (The Burma road is the maintenance road for the north unit irrigation canal and is very securely gated and locked so do not wast your time trying to see if you can get to it with a vehicle).
Smith Rock is a world-famous rock climbing destination and is stunningly scenic. There are great day hikes around the park. The campground there has good views of the rock but it could be full with climbers. The Skull Hollow campground is not very scenic and spartan but free. Expect to share that one with horseback riders, ATVers and climbers on a budget. There are no stores real close so you may want to stock up before you drive out to camp. There are good restaurants and a grocery store in Terrebonne which is 10 miles away. The nearest showers might be the public pool in Redmond. The Crooked River does not look appealing to swim in. It is brown and smells like fertilizer most of the year. It is excellent whitewater kayaking the few times a year when it comes up, however. You would never know this from most of the slack water around the park.
The Cole and Warner Loops have not been added to the maps below yet. If you manage to GPS these send a file and I can add it.