Take a spin at a legendary Bend riding spot
Phil’s Trail System Warm-up
Cog Wild,
Ride Ambassador
Length 15 Miles
Difficulty
Moderate i
If you know mountain biking in the Pacific Northwest, you know Phil’s—Phil’s Trailhead, that is. Located just a couple miles from downtown Bend, it’s the perfect place to get acquainted with the twists-and-turns-through-the-pine-trees experience that Central Oregon’s known for.
Even the expanded parking lot fills up fast at Phil’s, so ditch the car and bike there on the convenient path that runs alongside Skyliners Road. You can’t miss the large trailhead, which offers restrooms and lots of signs to help you select the route you want.
In this case, we’re taking Ben’s Trail, which flows uphill in quintessential Bend style—a gentle moderate-grade climb through lodgepole and ponderosa pines. One of the area’s draws is that many trails don’t require huge quads and huger lungs. They’re fun rides for beginners, families and anyone else who wants to breathe in some fresh mountain air.
After five miles, you’ll cross Forest Road NF-300, as well as another trailhead on your right. Hop onto Forest Road NF-310 and keep climbing for another 1.5 miles, then turn left onto famed Phil’s Trail, where you’ll want to gear down for a final steep climb. Once you hit the top, catch your breath for a minute by inhaling some of that incredibly pine-scented air, fuel up and get ready for a truly fun descent.
The first downhill section is the steepest, with just a few rocky sections. The rest of the descent stretches out over 7 heavenly miles that you can coast or sprint down, to your heart’s desire. Just make sure you stay on Phil’s Trail the whole way—there are lots of signposts to guide you, and Phil’s is a one-way trail so that you don’t have to worry about bikers or hikers coming your way.
Once you’re back at the trailhead, simply hop back on the roadside bike path for a few-minute ride east into Bend. Skyliner Road turns into Galveston Avenue, which is loaded with popular food and drink options, from Bo’s Falafel Bar to Sunriver Brewing Company and Kanona Café. Be sure to ask the customer next to you which trails they like at Phil’s—odds are they’ll have an idea or two.
Riding Season
Spring through late fall is best, depending on snowpack. Ask about trail conditions, which can be muddy in shoulder seasons, at one of the many local bike shops.
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In Oregon, a bicycle is legally considered a vehicle, and the same Oregon road laws apply. Please “be seen” and practice safe riding. Vehicle traffic, farm equipment and narrow shoulders exist on many Oregon roads, and you may find that construction projects, traffic or other events may cause road conditions or signage to differ from the map results, ride descriptions and directions. For travel options plus weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941. Routes listed on this website are for informational purposes and intended as a reference guide only.
About The
Ambassador
Cog Wild
Cog Wild has been bringing people together for fun adventures outdoors for 15 years. From their headquarters in Bend, they offer multi-day and daily tours for families and small groups, skills clinics and shuttles to Dutchman, Swampy and Wanoga Trailheads. Their guides and coaches are local and professional: they love to get people on the trails and to share the natural and cultural history of the region.