Westside Tour

5 Star Route / Published September 2017

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 Westside.  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.

What we love about his route is that it is chocked full of Bend history, culture, and heritage and has some amazing river and mountain views. There are kiosks for the first schoolhouse in Bend, the history of the irrigation dams, some old logging and mill implements, and a number of pieces of art and sculpture.

Adventure / Gravel Route

Loop: 25 miles / 1400 ft gain
– Surface: ~ 40% gravel, 10% single-track, 20% paved bike path, 30% paved road
Technical Difficulty: Easier
Tire Size (recommended minimum): ~ 40 mm tires
eBike Friendly: No
– Location: Bend, OR

RideWithGPS | Strava | GPX file | Cue Sheet | Legend

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).

And if the weather is touch and go, this is a perfect route. It is really easy to bail out and be back to town in a flash.

The Start

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

Terrain & Riding: What to expect …

The route is fun, close to town, relatively flat, and a mix of paths, trails and road. Expect to encounter others on the trails, remember to give way. The terrain is a mix of urban and national forest, with a number of scenic river and mountain views.

Be ready to test your navigation skills. There are a number of tricky turns, ones that are easy to miss, thus zoom way in on your navigation device. Way in!

Highlights & Anchor Points

Drake Park / ~ The Start

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.

Shevlin Park to Phill’s Trails / ~ mile 8.9

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.

Back to Town / ~ mile 18.5

You then catch the bike path back towards town, which winds you into a 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. 

Technical Difficulty[what this means]

  • Riding Difficulty: Easier
    There are a couple of short single-track segments that are rated mountain bike easy.
  • Navigation: Challenging
    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.
  • Locale: Urban Forest
    This ride is mostly within the city limits.

Food & Water

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

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

  • March 2022 / Updated for Gravel Adventure Field Guide.
  • 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.

Love Where You Ride!

We encourage you to stop and see the many pieces of art and sculpture along this ride. For a sample, see the photos at the end of slide deck to left.

To learn more about public art in Bend, check out Art in Public Places.

The Ride!

Two Bits Sculpture

An interview with the creator, Craig Congleton. At ~mile 23, at the far end of the wooden log deck bridge.


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.

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.

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