Westside Tour

5 Star Route

This is a 5 Star Route, meaning that it is a highly curated, premier riding route.

The West Side Tour is just that …. A quick tour of Bend’s West side.  It’s a lot more urban than we normally ride, but we’ve tossed in enough forest roads to make it an honest gravel route. Bring your silly hat because you just can’t take this one too seriously. There’s enough little girls on pink bikes to make you laugh, some of them will be on the terrain park at the Phil’s Trailhead. 

Adventure / Gravel Route

Loop: 26 miles / 1400 ft gain
– Surface: ~ 50% gravel, 5% single-track, 20% paved bike path, 25% paved road
eBike Friendly: No
– Location: Bend, OR
– Date Published: September 2017 (Updated: July 2021)

Terrain & Technical Riding Difficulty[what this means]


Technical Difficulty. There are a couple of short single-track segments that are rated mountain bike easy.

Navigation. There are a number of turns along the route, and it is easy to miss a turn, but it also easy to correct the mistake. This is a great course to test and refine your navigation skills.

Remoteness. This ride is mostly within the city limits.

When we like to ride this …

This is a go to route for us Bend locals. It goes most of the year, except when we there is snow in town. We like this route outside of tourist season. If done during the summer, and early start is recommended (prior to 8 am).

The Start

Drake park near the historic green “wagon wheel”.
Lat / Long: 44.058967, -121.318233


Red = paved road
Brown = gravel / dirt road or double-track
Blue = single track
Purple = paved bike path / roubaix

For help with GPS files, the RideWithGPs mapping app and to learn how to download our routes for free, see the “Using Our Rides” page.

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. 

Food & Water

@ mile 0, downtown Bend. @ mile 20.5, the cafe at the Loge Bend. @ mile 24, the Old Mill.

Ride Notes

~ 40 mm tires are about right for this course.

Ridden and Reviewed by …

Gravel Girl / Team Dirty Freehub

She loves a good day of gravel like most people like a good book. She’s always amused by the outdoors and the wild adventures. Gravel Girl is a Co-Founder of Dirty Freehub.

Captain O / Team Dirty Freehub

He should have “Never Stop Exploring” tattooed on his chest! He loves adventures on bikes and is a Co-Founder of Dirty Freehub.


Revision History

  • July 2021 / Put route guide into new tabbed / multi-media format.
  • January 2020 / Added pictures, added to route description.
  • September 2017 / Original Post as 5 Star route.

Get Involved!

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The Ride!

Coming soon…


Multi-Use Trail Etiquette

The River Trail and the Shevlin Park Trail are Bend Parks & Rec multi-use trails. Make sure you know who has the right of way.

Roundabout History

Roundabouts are a unique part of Bend’s history. The first roundabout was built in 1999. Today there are over 40 in the city. Learn a bit more about them in this podcast.

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