The Pinnacles Trail at Cottonwood Canyon State Park in Condon, Oregon is a moderate 10.5-mile out-and-back trail that features beautiful views as it traverses the floor of a large canyon.
This is the quintessential eastern Oregon sage-steppe desert river canyon hike. The main hike follows along the Pinnacles Trail, but a short extension at the start makes the hike a bit better.
From the large main visitor and day use parking (the first one you come to upon entering the state park), follow the path along the parking area across the entrance road, then follow that trail up to the junction with the Sage Steppe Trail. All that matters is that you connect with the Sage Steppe Trail from one of the first major parking areas before the campground–the way you take to it matters far less.
Turn right onto the Sage Steppe Trail, following along and above the west side of the entrance road leading to the campground and hike-n-bike parking area. The road is pretty much out of sight most of the time. This trail is singletrack, and meanders along a sagebrush steppe desert landscape, set far back from the river.
Approach the campground, then pass the short spur for the hike-n-bike trail and parking area to the right. Then reach the official trailhead for the Pinnacles Trail at the far end of the park road. Take the Pinnacles Trail, which is an old jeep road converted to trail.
The trail soon carves its way into the side of a sheer cliff, as you walk along the trail with basalt canyon walls below and above your head. This goes on for a bit, then fades out. Not long after that, reach a four way junction. The trail to the left is the D and H Trail detour. Take this trail to follow above the canyon, for a much better vantage point of the river and surrounding canyon. The trail to the right is the River Loop Trail, which is a detour along the river bank before connecting back up with the Pinnacles Trail. Take either trail, or continue along the Pinnacles Trail, as both trails will eventually reconnect back up with the Pinnacles Trail.
After taking the D and H Trail (or the River Loop Trail) and reconnecting with the Pinnacles Trail, follow the main trail for a long ways as it rounds around a "gooseneck" feature on the west bank of the river. The trail continues on around the bend, as the canyon seems to narrow up somewhat. The trail gets increasingly narrow and rocky, before passing under a series of basalt formations known as The Pinnacles. The Pinnacles are a series of basalt portions of the canyon wall that are more separated from the main canyon wall.
After passing under the Pinnacles, the trail eventually reaches a small clearing and a closed gate. This makes a good lunch spot. The trail does seem to keep going after the gate, but it gets increasingly hard to follow and covered in vegetation after just a few hundred feet. Turn around and head back the way you came. When you reach the two sets of detour paths, consider taking the one you didn't take on the way in.
Parking can be found at the direction coordinates provided. This lot is the first main lot upon entering the park and is large enough for about 20 vehicles. There's another parking lot, 100 feet south of this lot, which can also hold about 15 vehicles.
If you want to bike this hike, the only portion of this hike that allows bikes is the Pinnacles Trail, not the Sage Steppe Trail.
Notes about Water, Snakes, and Poison Oak:
There are no creeks or clean water sources along the trail, although the campground may have it, and there is access to the John Day River in places (with filterability questionable from all the farm pollutants above the canyon and surrounding the river).
There may very likely be Poison Oak in places. There are also definitely rattlesnakes. Be especially cautious around the Pinnacles formation, where the trail narrows and scrambles over rocky areas. Also be on the lookout on the narrower D and H Trail, and the River Loop Trail.