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Bend it like, well... Bend

01 June 2014

by Helen Edwards

The thought “I could live here” popped into my head as we drove into the town of Bend, Oregon. Not too big, not too small, high desert climate, good foodie options, a craft brewing scene that’s perhaps the best in the USA and phenomenally good mountain biking. I mean phenomenally good.

In my mind, a great mountain bike destination needs to sport the full range of technical options – green to double black. Check. It needs trails that provide a breadth of approachability – old school, backcountry exploration and close-to-civilization loops. Check. It needs some killer hill climbs for that real test as well as long rolling terrain to indulge a rest day or an enduro-inspired high-exertion descent. Check. A great mountain bike destination needs world-class scenery, a chilled out off-piste bike vibe and a palpable sense of mountain biking being deeply rooted in the local community. Check, check, check. One day, perhaps, it could be an option to live with this abundance of biking love but for now, it’s an eight-hour drive from the Bay Area.

Bend, Oregon, lies on the eastern side of the Cascade mountain range in central Oregon. It’s a four-hour drive from Portland or a short flight. There are good services and plenty of accommodation and eating options from top shelf to camping.

Once in town, make a stop to pick up the maps you’ll need - either a bike shop ( Crow’s Feet Commons in downtown Bend is our favourite) or REI. There are a range of specific mountain biking maps containing suggested loops and ride directions with good information regarding the technical difficulty and times/mileage.

There is literally so much riding that it can be hard to separate the unmissable from the optional. Here are some ideas for making the most of a few days in Bend.

Day 1. Close to Bend, 2-3 hours

Stretch out the legs and leave the car in town. Many of Bend’s most famous trails, such as Phil’s, can be ridden from town. The gentle slopes that characterise the eastern side of the Cascades are at their most gentle on these lower trails. Get a feel for Bend’s trail conditions (often powdery dusty in summer) with a quick spin up Ben’s to the helicopter pad and back down Whoops and Phil’s to finish at Phil’s trailhead. This is classic Bend riding with some moderate technical sections, a few obstacles but primarily swoops, jumps and corners. Lots and lots of carved corners. Trails in the Phil’s Canyon area have recently been designated one-way only so check with a local for any recent changes.


Suggested brew stop: Deschutes Brewery Public House in downtown, the original in Bend with a darn good house-baked pretzel and cheese. The bartenders have a good knowledge of Bend’s bike and social scene. A great place for a first night’s orientation.

Day 2. A bit out of Bend, 3-5 hours

Pack a lunch and plenty of water and drive up the Cascade Lakes highway to Seventh Mountain Resort to park. Head up C.O.D. to Storm King and on up to the Helicopter pad. Follow Skyliners trail to Skyliner Sno-Park. There’s a tough climb up Tumalo Ridge trail to the view at Swede Shelter. Alternatively head up the upper part of Whoops Trail and around Sector 16 to the shelter but beware traffic coming down this particularly fast section of trail. Complete Swede Ridge loop by following signs to Swampy Lakes Shelter. From there, head up the lower section of Flagline to Flagline Tie and then to Swampy Lakes Sno-Park via Ridge Loop.

Then duck onto the Cascade Lakes Highway for 200 meters (east/downhill) and into Wanoga Sno Park. At the east end of the parking lot (Steve Larsen Trailhead) take Tiddlywinks. Tiddlywinks is one of the top trails in the area - beautifully built, flowing and great for all skill levels. Either continue on Storm King to Conklin Rd and then, at the road, turn left to get back to where you parked. Or head up Larsen trail and exit via Tyler’s Traverse, a new trail that’s building a strong fan base.


Suggested brew stop: Crux Fermentation Project. A dramatic sunset view of the day’s trails, a vibrant scene with a good selection of hearty post-ride sandwiches on the menu. Oh, and excellent beer.

Day 3. Flagline and higher into the Cascades. 3-7 hours

The reason to visit Bend in late summer/early autumn is Flagline. Perhaps one of the best-kept secrets in the mountain bike world, this trail has a relatively short season as it’s closed until 15 August each year to protect the elk calving habitat. Come mid August though, elk are scarce. Cog Wild runs shuttles every half an hour or so. After a short, but honest, climb there are as many miles of downhill as you’d care to ride. As much as all the way back to Bend (more than twenty miles) or as little as seven to the Swampy Lakes Sno-Park for a pick up.

However, the primo ride is a loop. It’s hard, it’s steep, it’s long, and is peppered with dozens of spectacular waterfalls and isolated, pristine scenery.

Park at Skyliner Sno-Park and take Tumalo Creek Trail to Tumalo Falls. The Falls themselves are dramatic but there are better to come. Join North Fork Trail (uphill only). Go up, up, up. Don’t get so focused on nailing the climb that you forget to stop and check out the numerous waterfalls along the way. Cascade mountain water is some of the purest in the world and Tumalo Creek knows how to show it off.


At Happy Valley, if you’ve had enough and want a bail out option, turn back to Tumalo Falls via Metolius/Windago and Farewell Trail. Otherwise, keep going with more climbing up Happy Valley and Metolius/Windago towards Dutchman Flat. Use Meadow Trail to connect with Flagline. The trail will get busy with the shuttle-users entering from a nearby drop off point (Dutchman Sno-Park) near Mt Bachelor Ski Area.

At the summit of Flagline, there’s usually a small crowd gathered. It’s good etiquette to give each rider a bit of space on this long, extended and super fun descent. To complete the loop, head down South Fork Trail to rejoin Tumalo Creek Trail. The descent on the singletrack along the river is fast and furious. By the time you get back to your vehicle, over 2000ft of descending will seem to have flashed by and you’ll wonder if there’s time to do it all again before dark.

Suggested brew stop: Crow’s Feet Commons. Perhaps the best place for a relaxed, all-inclusive experience. Excellent selection of the finest local brews, brilliantly curated schwag, terrific, like minded biker owners and staff, comfy chairs which feel good on a stiff lower back, a chilled out sunset spot on the river with a glimpse of Mt Bachelor and a mellow, locals’ scene.

Nitty Gritty

  • Trails are generally muddy and unridable in spring (and often covered in tree fall from heavy winter snow). Summer and early autumn are the best times; fallen trees have been removed and trail surfaces are hard packed. 
  • This is one destination where renting bikes is a good option if you don’t want to travel with the steed.Crow’s Feet Commons andCog Wild both rent high-end full suspension bikes for a very reasonable price, ideal for Bend’s swoopy fun trails. 
  • Bees are everywhere in the forests. They never seem to sting but they look like they could. Be prepared, it’s a bit like flies in Australia – unrelenting. 
  • There is very little user conflict. Everyone is friendly and mountain bikers rule. It’s not California with the issues with equestrians, hikers and park rangers with radar guns. The speed limit in Bend is your ability to corner. Still, ride by the code and more trails will open. 
  • COTA (Central Oregon Trail Alliance) is a non-profit collaboration that oversees trail development and maintenance. Consider joining ($30) or making a donation to help support their great work.
  • Avoid getting lost by visitingAdventure Maps Inc.
  • Gear, beer and personal knowledge:Crow’s Feet Commons = best hang out in town, combining relaxed space, views, coffee, bikes and beer (really) and with a motto of “success is measured in laugh lines”.
  • Coffee and Sweets:Lone Pine Coffee Roasters. Do not miss the waffles, made fresh Friday through Sunday. You’ll be spoilt - reproductions from other cafés just won't cut it, ever.
  • Pizza and local emersion:Jackson’s Corner. You won’t see many tourists here; it’s very much a local family joint. Excellent pizza and a terrific Friday night chaos as a local band jams in with a crowd of happy families.
  • Quaint and slightly odd-ball:McMenamins St Francis Catholic School, now a pub-hotel-brewery-indoor soak pool.