Mountain Biking in Bend: A Guide from Beginner to Advanced

Bend shows up on best-mountain-biking-towns lists the way Bend shows up on most best-of lists: often and near the top. The trail network here has been built over decades by a community that takes riding seriously, and the result is one of the most varied and well-maintained singletrack systems in the Pacific Northwest. September and October are genuinely the best months to ride it, cool enough to push hard, dry enough to be fast, and empty enough that the trails feel like they're yours.

For beginners: start at Deschutes River Trail

The Deschutes River Trail is flat, scenic, and forgiving enough to build confidence without consequence. It's not technically a mountain bike trail in the traditional sense, but it's where a lot of Bend riders get comfortable on the bike before moving into more technical terrain. You can ride sections of it on a hybrid or a hardtail and feel good about your morning.

Getting started on singletrack: Phil's Trail

Phil's Trail, on Bend's west side, is the entry point to the larger trail network for most new riders. The beginner-friendly sections are genuinely approachable: rolling terrain through ponderosa pines, clear sight lines, and enough variety to stay interesting without being punishing. As your skills build, the network branches into progressively more technical terrain. Most Bend riders have logged hundreds of hours on Phil's Trail and still ride it regularly.

Intermediate riding: The Funner / Tiddlywinks network

Once you're comfortable on rolling singletrack, the Funner and Tiddlywinks trails open up a more technical and rewarding experience. Flow sections, optional features, and terrain that rewards commitment without demanding it. This is where riding in Bend starts to feel like what the reputation suggests.

Advanced riding: Whoops and Maston

The Whoops trail is one of Bend's most beloved advanced descents, a fast, loose, pumpy line that rewards bike handling skills built over time. The Maston trail area in Redmond offers desert singletrack with a completely different character: open, exposed, technical in a different way, and worth the short drive. Advanced riders who want variety between the two systems have weeks of riding without repeating a line.

Smith Rock for something completely different

The trail network around Smith Rock includes mountain biking on designated trails with a completely different landscape than Bend's ponderosa forest. Volcanic rimrock, canyon views, the Crooked River below. It's not the same kind of riding as the west side trail network, but it's exceptional in its own way and a great full-day option when you want a change of scenery.

A few things worth knowing

• The trail system is managed partly by Bend Parks and Recreation and partly by the Central Oregon Trail Alliance (COTA). Trail conditions, closures, and new additions are tracked on the COTA website and app. Check it before you go.
• Wet trails close. Riding wet singletrack in Central Oregon damages it, and the community takes that seriously. After rain, give it 24 to 48 hours.
• September and October are prime season. The trails are dry, the temperature is ideal, and the crowds are the lightest they've been since spring.
• If you're new to Bend's trails, Cog Wild offers guided rides and shuttles. It's the easiest way to get oriented quickly.

Mountain biking is one of those things that brings people to Bend and keeps them here long after they expected to leave. It's baked into the identity of the town in a way that takes most newcomers a season to fully understand and then can't imagine living without. If you want to know more about what everyday outdoor life in Central Oregon actually looks like, we're always happy to share it. Reach out anytime.