Skull Hollow Road: Easy

Despite being only a 28-mile loop, which is primarily a paved bike route, Skull Hollow Road is considered moderate due to the trail being on service roads and having roads with a steep grade of 15 %. Between miles 10 and 12, riders will climb nearly 1,000 feet. The path will provide riders views of Smith Rock, over the Crooked River (high) bridge and Grizzly Mountain.

Twin Bridges: Moderate

An evenly split mixture of paved and gravel roads, the Twin Bridges Trail is a 40.9-mile loop that begins and ends at Compass Park in Bend. The route goes through the Miller Tree Farm, Shervin Park, Jonson Market road, Sisemore road, Tweed road, Dusy Lane, and across the Deschutes River. Considered an easy route by dirtyfreehub.com, bikers will experience a 1,817-foot elevation climb.

Gravel Cracker: Challenging

With an 85-mile loop and 5,200 feet in elevation gain, GravelCracker 85 is a challenge for even seasoned cyclists. The trail starts and ends in Creekside Park in Sisters. The path climbs to Round Lake, goes around Suttle Lake, up to Black Butte. There are two climbs on the trail that exceed 1,000 feet in elevation.