Want to tour the state of Oregon on bikes? Plan your road cycling vacation to Bend Oregon and Central Oregon. We’re known worldwide for amazing road cycling opportunities. From mountain biking to road biking, and everything in between, Bend’s reputation as “Bike Town U.S.A.” is well-deserved.
At the heart of this Oregon cycling mecca is the Three Sisters Scenic Bikeway, a collection of premier road cycling routes that connect the communities of Central Oregon and provide premium and scenic road cycling opportunities to visitors and local residents alike. Route descriptions, maps, and everything you need to know to explore the Three Sisters Scenic Bikeway are listed below. If you’re setting out on your own, be sure to visit this website before you saddle up to get all the latest bike news, and to learn about new routes being added. For more information, visit us at the Bend Visitor Center in downtown Bend to get the inside scoop.
Several routes within the Three Sisters Scenic Bikeway have been officially designated by the State of Oregon as Oregon Scenic Bikeways (see designations below). These routes represent the most scenic road cycling routes in Central Oregon. You can learn more about the Oregon Scenic Bikeways program by clicking here.
Road Cycling in Oregon – Resources
The entire state of Oregon offers amazing cycling opportunities, and there’s no better resource for information than the Ride Oregon website. Learn more about premier cycling opportunities across the beautiful state of Oregon cycling routes and along the Oregon Scenic Bikeways.
Distance: 36.29 miles (round trip) Elevation Gain: 1,073 vertical feet
Starting and ending at Drake Park in the heart of downtown Bend, the Twin Bridges Loop is one of the most popular and scenic road cycling routes in Central Oregon. The Twin Bridges Loop covers 36 miles of rolling terrain and offers breathtaking views of the snow-capped Cascade mountains, rolling forests, and inspiring high desert terrain.
Distance: 36.69 miles (one way) Elevation Gain: 597 vertical feet
Starting in the “Old West” town of Sisters, Oregon and ending at Smith Rock State Park outside the small town of Terrebonne, this route takes riders past a variety of historical sites, shows the gentle curves of the Deschutes River and frames spectacular views of the Cascade Mountains, ending with the dramatic walls of Smith Rock State Park.
Distance: 6.64 + miles Elevation Gain: All loops are relatively flat with between 187 and 300 total vertical feet of climbing.
This series of loops begins and ends at the historic Camp Sherman Store and Fly Shop on the stunning Metolius River. These loops vary in difficulty from a short family-friendly ride to a combination of loops to create an extensive 20+/- mile ride. With a few moderate exceptions, most of the riding is flat or rolling and perfect for a family bike ride.
Distance: 37.91 miles (one way) Elevation Gain: 2,191 vertical feet (add an additional 4,000 vertical feet if you ride back to Sisters)
The 38 mile McKenzie Pass ride is without a doubt the most spectacular bike ride in the entire state of Oregon. The ride begins at the Village Green Park in Sisters, Oregon, along Oregon Route 242, which is a stretch of roadway included on the U.S. Register of Historic Places. The route heads west past hay meadows and ascends 2,000 feet through Ponderosa pine forests. The road follows an 1860s wagon route, emerging from the forest at Windy Point and revealing a view of Mt. Washington and a 2,000-year-old lava flow. The 25 mile, 4,000 foot descent snakes down exhilarating switchbacks to the dense, verdant Cascadian forests and rushes out over the McKenzie River. It is these dramatic transitions through such diverse natural environments that define the uniqueness of this Oregon bikeway.
Distance: 44.8 miles (round trip) Elevation Gain: 3,474 vertical feet
The Bachelor Party Out & Back is the classic ride from Bend to Mt. Bachelor and back. While not for the faint of heart, this 44.55 mile out & back route along Century Drive is one the most popular and scenic road cycling routes in Central Oregon. The route starts and finishes in Drake Park in downtown Bend, and begins the 22 mile gradual ascent to Mt. Bachelor Ski Resort shortly after crossing the city limits. The climb from Bend to Mt.Bachelor winds through the Deschutes National Forest along the Cascade Lakes Scenic Highway offering breathtaking views of the Cascade Mountains and surrounding Buttes. The entire route was repaved in the summer of 2012 with velvety smooth asphalt and wide bike lanes. Take a rest after the 22 mile climb at the Mt. Bachelor Ski Resort parking lot, and prepare for the exhilarating descent back to Bend.
If you’re hankering for a really long ride through beautiful high desert landscape, the Prineville Century Loop will deliver the goods. This 98-mile round trip takes cyclists through the rolling high desert east of Bend, past the charming western town of Prineville, then along the Crooked River and Prineville Reservoir. This route is ideal for those cyclists who are interested in a longer ride without sacrificing scenery.
Bend to Sisters Via Twin Bridges & Sisters to Smith Rock Scenic Bikeways
Distance: 41.1 miles (one way) Elevation Gain: 3,599 vertical feet
Starting and ending at Drake Park in the heart of downtown Bend, the Twin Bridges Loop is one of the most popular and scenic road cycling routes in Central Oregon. The Twin Bridges Loop covers 36 miles of rolling terrain and offers breathtaking views of the snow-capped Cascade Mountains, rolling forests, and inspiring high desert terrain.
Distance: 35.5 miles (one way) Elevation Gain: 2,689 vertical feet
If you’re in Bend and want to take a beautiful bike ride and explore Sunriver, this route is your chance to be efficient with your recreation. You’ll climb the popular Cascade Lakes Scenic Byway toward Mt. Bachelor through the Deschutes National Forest. From there you’ll roll through more Ponderosa pine forest, cross the river, and reach Sunriver at mile 35.5 where you can enjoy fantastic restaurants, shopping, or even surf a standing wave!
Distance: 29.5 miles (round trip) Elevation Gain: 2,782 vertical feet
The Madras Mountain Views Scenic Bikeway is a rural loop, starting and finishing in Madras, Oregon. You’ll pedal through a sage and juniper ecosystem, showcasing basalt palisades above the Deschutes and Crooked Rivers, along with the farms and ranches of Jefferson County. The bike ride offers stunning views of the Three Sisters, Mt. Jefferson, Mt. Hood, and Three Finger Jack, and passes by The Cove Palisades State Park.