Not far from Bend, just East of La Pine you’ll find the Crater Rim trail. The trail starts at the Paulina Lake Trailhead (a Northwest Forest Pass is required, or you can pay at the kiosk). Circling the caldera counter clockwise, you’ll first climb NF-500 Road towards Paulina Peak.
Near the summit, the trail dives off to the right and is a combination of single track and winter snow-mobile routes. For a bonus view, ride past the trail junction to the summit where you’ll have an amazing view of East Lake, Paulina Lake, and the Cascade Range.
After a fun bit of downhill, you’ll start to climb again to the upper rim of East Lake. The reward is more great views — and a long downhill section back to your car.
Because of the elevation (over 6,300 feet) the Crater Rim stays covered in snow until late into summer. So early Fall is prime time at Paulina. There is an optional ride from the rim down Swamp Wells, but it’s most likely going to be full of deadfall.