The best gravel ride in Bend?

Bend Oregon contains a hotbed of gravel cycling routes. with so many choices it can be difficult to know where to begin. this ride should be at the top of your list.

With gravel roads leading every which-way out of town it can be daunting to know which ones to steer your bike down. Which roads lead to interesting places? Do those connect to others to make a loop? Are there roads that leave you at a dead end gate with private property on the other side? You could spend years pouring over maps, researching every twist and turn, discovering the successful routes and marking off the ones not worth riding twice. Or you could save yourself the trouble and check out Dirty Freehub.

Dirty Freehub is a local non-profit organization that has curated an extensive collection of gravel routes in the Central Oregon area and beyond. They’ve spent countless hours pedaling down (and back from) those dead end roads, finding the connector routes, and putting all that saddle time together to present gravel rides that are enjoyable and easy to follow. On a recent Sunday afternoon my partner and I pumped up the tires on our gravel bikes, threw snacks, windbreakers and lights (we like to meander) into our frame bags and set out to explore one of Dirty Freehub’s “5 Star” routes that begins and ends at the west edge of town.

We chose the route “4 Boys”, a loop listed as 36 miles with about 2,100 ft of climbing. We figured it sounded like a nice distance to spend some quality time outdoors, enjoying the nearly perfect fall afternoon in Bend. And with a pretty solid knowledge of the main roads and trails west of Bend, I also knew we could cut it short at multiple points if darkness befell us too soon and we wanted to get home for that well deserved pizza.

The route starts at the edge of Bend in the well-known Phil’s Trail network. The singletrack is mellow and easy to follow as it winds through an open pine forest. Vegetation removal by the West Bend Project has created a clear understory and increased fire safety, while looking a bit raw until the grasses and flowers regenerate.

After a few miles the trail leads to a network of gravel roads, and following these south delivers you to one of the few bridges across this section of the Deschutes River. We stopped for snacks here (bagel anyone?) and took in the beauty of the evening light over the river, witnessing fish rising and birds darting to and fro, both seeking insects as their own snacks.

Bagel consumed, we continued onwards, exiting the bridge and entering the paved walking and riding trails in the resort community of Sunriver. A map is just as necessary here as out on the forest roads, as the paved paths are a literal maze. We navigated through Sunriver without pausing (although this is a nice place to stop for a meal at the excellent Sunriver Pub ) as the light was falling fast and we still needed to pedal home to Bend.

Departing Sunriver, the route leads north and back across the Deschutes River on another bridge, this one being along the historic Shevlin-Hixon railroad. Timber was floated downriver to this point and then loaded onto railcars and taken to the mill located at the modern day aptly named Old Mill District of Bend.

At this point we turned on our bike lights, stopping for a moment at the beautiful Benham Falls (no photos this time, it was nearly dark) before departing the “official” route. We chose to follow forest roads and pavement home seeking out that well-deserved pizza. The actual “4 Boys” route continues along the river past Benham Falls, following sections of the Deschutes River Trail back into town. It is undoubtedly a more scenic route than the way we chose to get back to Bend, but darkness had fallen and pizza was calling.

So is this indeed the best gravel ride in Bend?

Well every ride is different. Even the same route never contains the same experience twice. But on this day, for us, the “4 Boys” route was exceptional. I encourage you to give it a ride. And maybe try a few of the other Dirty Freehub routes as well, and then make your own determination. Happy trails.