The Westside Tour bike route is exactly what it sounds like, a quick and scenic gravel tour of Bend’s charming Westside.

This 26-mile loop starts at Drake Park, winds through town along the Deschutes River and up Awbrey Butte before heading into aromatic ponderosa pine forests. A fabulous mix of terrain from pavement to gravel, not too much elevation gain, and a doable distance make Westside Tour a popular ride for those new to gravel biking or perhaps looking for a Sunday morning pre-brunch ride.

Open almost year-round except when snow’s on the ground or it’s mud season, you can easily enjoy this ride on a crisp fall day to an early summer morning to beat the heat. And because the loop ends right back in town, why not grab lunch in downtown Bend or quench your thirst with a cold hoppy beverage at one of our local breweries.

What better way to enjoy a bit of urban flare, various terrain, and a mellow gravel ride that goes right through Bend’s picturesque backyard than riding Westside Tour.

Distance: 26 miles
Difficulty Rating: Easy+
Elevation Gain: 1400 vertical feet
E-Bike Friendly: No
Start Location: Drake Park Bend, Oregon
Surface: ~ 50% gravel road / double-track, 5% single-track, 20% paved bike path, 25% paved road

Ride Details

The route is fun, close to town, and a mix of paths and trails with a smidge of roads. You start out in downtown Bend, in the historic Drake Park. You then pass by First Street Rapids and take the River Trail around Awbrey Butte with nice views of the mountains. When the River Trail ends, you will take paved roads up the backside of Awbrey Butte and head out to Shevlin Park. Then you meander through Shevlin Park and then on a few paved roads to reach Skyliners Road and then over to Phil’s Trailhead Parking Area (which is the start of an extensive mountain biking area). Here you are on gravel roads that will loop you to Century Drive. You then catch the bike path back towards town, which winds you into gravel road, paralleling Century Drive. You will drop down into the Old Mill District and follow the Deschutes River, then slice through a historic neighborhood to take you back to Drake Park.