“The singletrack is great, but the views are even better.
— Chad Hartley
The road is closed much of the year. Check conditions before attempting. July to September is probably your best bet.
This is a fun loop trail with some wonderful views. The terrain varies between loose dirt/pumice and firm fast singletrack. It's presented here as a loop requiring just 1 vehicle, but a shuttle is pretty easy if you want to skip the 3 mile gravel road climb. Counter-clockwise is the preferred route.
Need to Know
This is really closer to La Pine then Bend. Make the extra trip up to Paulina Peak before hitting the singletrack for a great view. This can easily be shuttled by parking one car at the lake and another up near Paulina Peak.
The final descent used to be a lot more technical, but trail work has smoothed it out. Bummer. Check out the obsidian flow which has a short hike through it.
There are some hot springs at East Lake for a little post ride soak. You can also find a couple natural slides in Paulina Creek on your way back down. There are guided 1/2 day trips that take you to them or you can do some research and find them yourself.
As displayed this ride starts at the day use parking next to Paulina Lake campground, across from the forest service building. The first 3 miles is up a gravel forest road for a great warmup. Most cars are considerate, but keep your eyes open.
The trail has a small sign and starts on the right side of the road. Pay attention because it's easy to pass. You can continue another mile or so up to the Paulina Peak viewpoint for a photo opportunity. The beginning of the singletrack is a bit steep and typically pretty loose with some exposure on the right. You'll drop in to the forest as you wind around the back side of the crater.
At about 4.4 miles, stop for a photo op at the viewpoint. You'll drop back to the backside of the crater from here and undulate down through a lot of loose pumice to a crossing with Newberry Crater Road. This is a great place to join back up with your group!
From here to about mile 13.1, you'll slowly climb back up. Trails are a bit more firm from here out with the occasional loose pumice rock. At 13.1 you'll get another fantastic view after a short steep climb. The trail keeps climbing to the high point of the ride at about 15.8 miles. From here, the remainder will fly by as you descend down to the car over the final 3.5 miles. This can get very loose later in the year as it's used by horses. Otherwise it's not a very technical downhill and can be very fast.