Cycling routes connecting central oregon

It’s the hawk soaring above you as you descend down into the Deschutes River canyon. The alpenglow on the Cascades as you’re racing the sunset to get home in time for supper. It’s the other-worldly black landscape in every direction as you reach the top of McKenzie Pass Scenic Byway, amidst a sea of ancient lava. The golden cliff face, standing watch above the meandering Crooked River, as you reach your midway point at Smith Rock State Park. It’s road cycling in Bend, Oregon.

Whether it’s your first time riding road bikes in Bend, or your thousandth, adventure awaits. These roads have drawn riders from all around the world, both to compete in the many different road cycling events held in Bend each year and simply to enjoy this distinctive western landscape that we’re so lucky to call our backyard.

Sitting in the rain shadow of the Cascades, on the edge of the High Desert, the weather is mild and dry for the vast majority of the year. There are countless options for cool rivers and lakes to soak your legs in on a hot summer day, and dozens of spas either in town or at one of the world-class resorts around the area to warm back up after a cold day out.

The following is a curated selection of routes from the Three Sisters Scenic Bikeway, a collection of premier road cycling routes that connect the communities of Central Oregon and provide premium and scenic road cycling opportunities to visitors and local residents alike. To best highlight the many amazing road riding options here, we’ve compiled a list of several of our favorites, in no particular order.

Mt. Bachelor/Cascade Lakes Loop

Although the mountains are a critical piece of the allure of this region, the road cycling in Bend has surprisingly little concentrated climbing. Most recreational road cyclists love riding in Bend because of its more moderate elevation gain. It’s teeming with a handful of 5-20 minute climbs. But for those seeking more concentrated climbing, there’s the out-and-back climb to Mt. Bachelor. This route offers almost 3,500 feet of sustained climbing and starts right from downtown Bend. It covers 22 miles of pristine highway winding up through the Deschutes National Forest.

While this route may involve a challenging day of climbing, the extended descent down smooth pavement back to Bend ensures a refreshing reward for all your efforts. Looking for even more adventure? Try the 87-mile loop option that lollipops around Mt. Bachelor with 5,300 feet of climbing. This bonus option offers the same breathtaking vistas of the Cascade Mountain Range and incredible views of several of the subalpine lakes along the western flank of the Cascade Crest.

McKenzie Pass

Another primary climbing option in the area is the McKenzie Pass route just west of the town of Sisters. The more moderate, popular version of this ride begins in Downtown Sisters. You’ll start with a gentle warmup through Ponderosa pines for about 8 miles before the climbing intensifies. After the first switchback, the climb is on. You’ll find just one short break in a climb of 1,500 feet, with a manageable average gradient of 3.8%, leading up to the crest at Dee Wright Observatory. Just over halfway to the high point, the trees fall away to a vast 2,000-year-old lava flow, revealing jaw-dropping views of many of the Cascade Mountains. 

At the high point of the journey (5,187 feet), the Dee Wright Observatory stands alone as a distinctive landmark. Constructed in 1935 as a Civilian Conservation Corps project, it offers panoramic views of lava flows and surrounding peaks. Inside the observatory, openings in the rock construction frame each of the dozen or so surrounding peaks. On the roof, a bronze peak finder shows the names and elevations of each peak and nearby buttes as they stand watch over the sea of lava rock. After getting your fill of the scenery, look forward to a screaming, fast descent back down to the outskirts of Sisters.

Alternatively, a far more substantial day of climbing awaits those yearning for more, just down the west side of the crest. To add 4,000 more feet of climbing to this route, in an additional 46 miles, simply carry on after passing Dee Wright Observatory and descend to Belknap Hot Springs beside the roaring McKenzie River before turning back for Sisters. Enter the forest once more as you begin the serpentine descent down the dozen or more switchbacks of the historic highway 242, leading to the McKenzie River valley below. Pine trees atop the pass give way to the lush deciduous forest of the western slope, ripe with ferns, maples, oaks, and a handful of waterfalls just off the side of this route. This option makes for a very big day on the bike, by anyone’s standards, so please plan accordingly for hydration and fueling options, knowing that the only reliable option for restocking lies at the turnaround point at the Belknap Hot Springs Resort.

Whether you choose the longest option or the standard east side approach to the McKenzie Pass route, this is a spectacular option that really stands out as one of the top road rides in the region. The Oregon Department of Transportation generally opens the highway to vehicular traffic on the third Monday of June. While it can be ridden prior to it being open to vehicles, those who choose to bypass the locked gates and road closure signage do so at their own risk. There is heavy machinery working the road mid-week, and seasonal road maintenance is ongoing to prepare the route for opening day.

Twin Bridges Loop

One of the most accessible and most popular routes in Bend, the Twin Bridges Loop of the Three Sisters Scenic Bikeway loops from downtown Bend through the rolling terrain of the Tumalo farm country just north of town. Complete with 36 miles of vistas of the snow-capped peaks of the Central Cascades, several crossing of the Deschutes River and one more of Tumalo Creek, and just over 1,000 feet of climbing, this is an iconic Bend ride.

Crooked River Canyon

A very similar profile to the Twin Bridges Loop, this out-and-back route along the Crooked River starts and finishes in Prineville. The stunning canyon landscape along the upper portions of the river make it clear why this ride stands out as another of the officially designated Three Sisters Scenic Bikeway routes. From the vast ranches of Prineville, this ride follows the river upstream as it sweeps through an ever narrowing river canyon, cutting through impressive basalt cliffs as they emerge from the river itself. Campsites and fly fishing spots line this corridor, with plenty of great opportunities throughout for a creekside picnic in the shade and a trip to the restroom before heading back downriver to Prineville.

Sisters to Smith Rock

One more part of the Three Sisters Scenic Bikeway, the Sisters to Smith Rock route is another out-and-back route of around 36 miles each way. Starting and finishing on the boardwalks of the picturesque Western town of Sisters, the route winds its way out of the ponderosa forests and through the rangelands of the plateau before descending down to the Deschutes river crossing and eventually reaching its halfway point on the cliffside above the Crooked River. Whether or not you are planning to pause for a snack break under the trees at Smith Rock State Park at this point, be sure to take a moment here to marvel at the iconic sheer cliff walls shooting up from the river below. The scene has been depicted in many, many artistic renderings through the years, including the can of the Deschutes Brewery Twilight Summer Ale and even a handful of Hollywood movie productions. 

Of course, there are many more incredible road cycling routes in and around Bend than just those listed above. Stop by one of Bend’s many great bike shops for additional recommendations while you are grabbing some nutrition or spare gear for the journey. It’s hard to go wrong, but our recommendations for some of those most knowledgeable and close to the road discipline are the following:

• Sunnyside Sports
• Hutch’s Bicycles
• WebCyclery