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Bend, Oregon, in the foothills of Mt. Bachelor - courtesy of Bicycle Adventures
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Bend Breakaway

Bend, Oregon. 300+ days of sunshine. Bike, hike, eat, drink, play = 4 days of pure heaven.

Our Oregon Bike Tours

A Word from our Clients
The Bend Breakaway was everything I could have asked for and more! The food and beverages provided during the rides as well as the hotels and restaurants we visited were amazing. I have done bike trips on my own, and this is a much better way to do it. Well worth every penny. I am already planning my trip for next year!
Anne F.
Dedham, Massachusetts
Great experience overall - met like-minded fun-seekers and shared great rides, meals and fun. McMenamins Old St. Francis and Five Pine in Sisters were both amazing lodging choices! 
Brad & Gwen H.
Yorba Linda, California
Guides are professional, fun, flexible and knowledgeable. They really care about making our experience the best it can be. Great hotel choices & restaurants!
Abbe B.
Hillsborough, California
I love the fact that once the van picks me up all I need to be concerned about is how much I want to ride my bicycle - and what I want for dinner. I love how well we are taken care of! 
Tim & Sandra M.
White House, Tennessee

Bend Breakaway

Signpost near Bend, Oregon - courtesy of Bicycle Adventures Beer Sampler at Bend, Oregon brewpub - courtesy of Bicycle Adventures Five Pine Lodge, a guest favorite on Bicycle Adventures' Bend Breakaway cycling tour. Photo courtesy of FivePine Lodge. Jacuzzi tub at Five Pine Lodge, on Bicycle Adventures' Bend Breakaway cycling tour. Photo courtesy of Five Pine Lodge. Smith Rock State Park, as seen on Bicycle Adventures' Bend Breakaway Tour. Photo: Bicycle Adventures. Guests relaxing on Bicycle Adventures' Bend Breakaway Tour Oregon's Mt. Jefferson, as seen on Bicycle Adventures' Bend Breakaway Tour

Bike. Hike. Eat. Drink. Savor an urban adventure tour of Bend, Oregon - the ultimate cosmopolitan mountain town. Snowcapped peaks punctuate the high-desert skyline. Roads are dreamy-smooth. And the weather? Some of the best in Oregon! Do the math: 300+ sun-drenched days each year = nearly endless playtime! Ride the prairie. Hike to Smith Rock, one of the most renowned climbing spots on the continent. Ride up McKenzie Pass to see the volcanic minefield. Taste-test local microbrews. Spend two nights in Bend, the outdoor capital of the Pacific Northwest, and the last night at Five Pine Lodge, voted a TripAdvisor 'Top Five Hotels in the Nation.' 

Note: Watch a video overview of the Bend Breakaway tour! Click here.

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Meet in Bend. Ride 30 miles on impeccable roads from Dutchman Flat to Crane Prairie. Sample Bend's brews!

Bend, Oregon is an outdoor-lover's mecca. The combo of high desert climate and spectacular Cascade Range make for plenty of sun and fun. It's heaven for cyclists, runners, climbers, skiers and snowboarders. Oregon also takes terrific care of its roads. Pavement is smooth, shoulders are wide and there's very little traffic.

Meet us here for the start of your trip. Ride the smooth pavement of the Cascade Lakes Scenic Byway and Deschutes National Forest. Cruise from Mt. Bachelor's Dutchman Flat ski park downhill through pine forest and alpine meadows. Splash in the crystal waters at Crane Prairie Reservoir, a bird-watcher's paradise and one of the top rainbow trout fisheries in Central Oregon (record fish = 19 pounds!) Tonight: Sample some of Oregon's renowned craft brews this evening - our treat! Spend the next two nights at Bend's eclectic McMenamin's Old St. Francis School - a converted schoolhouse with a heated art-deco pool. 


Bicycle from Bend to Sunriver.

Bike more incredible roads today through high desert forest and past hints of craggy volcanic peaks to Sunriver. Have an ice cream cone, explore the village, then shuttle back toward Bend. If there's time, stop for a visit at either Lava Butte or the High Desert Museum. Dinner's on your own tonight in Bend; your guide will have plenty of options there. 


Ride from Bend to Sisters via Smith Rock State Park. Climbing lesson, anyone?

Bike to Sisters, Oregon today through some of the most sublime scenery in Central Oregon. Enjoy spectacular views of the snowcapped Cascade mountain range, rocky canyons, high-desert pastureland and the meandering Deschutes River. Watch for golden eagle, mule deer and river otter. Pedal the Three Sisters Scenic Bikeway to one of the Seven Wonders of Oregon: Smith Rock, a climber's mecca with over a thousand bolted routes. Sleep in luxury tonight at Five Pine Lodge, one of Tripadvisor's 'Top Five Hotels in the Nation.' 


Bike McKenzie Pass, which RideWithGPS calls "undoubtedly the most spectacular ride in Central Oregon." Then cruise down again for lunch and the journey home.

Enjoy one of Central Oregon's most remarkable rides today: the east side of McKenzie Pass. Ride from Sisters east through open woodlands dotted with lodgepole pine. Climb a gentle grade into the Willamette National Forest and up to the summit - where the scenery changes dramatically. The forest disappears and views explode into an incredible lunar landscape. Immense lava fields spread out on every side, leftovers from a volcanic eruption thousands of years ago. Snowy peaks slice the horizon. Hike the short trail to the Dee Wright observatory, hand-built from the lava rock by the Civilian Conservation Corps in 1935. Then cruise down again to Sisters for a finale lunch at Three Creeks Brewery. 

Make your reservation now or (800) 443-6060.

Bend Breakaway

Trip Details

Included Activities

Biking (bikes included), hiking, beer sampling


4 days - Sunday to Wednesday


All Levels


All meals included except 1 dinner

Daily Mileage

Standard route: average 30, range 25 50


Bend, Oregon (airport 16 miles north of Bend in Redmond)

2019 Departures

June 23.



Traveling Alone?

Single Room

As an optional extra, a person traveling solo on any inn-to-inn trip may reserve a room for his or her exclusive use. This will guarantee you a private room and private bath every night. Unlike other tour companies, if you're willing to share a room, there is no extra charge for coming solo, no matter when you sign up for the tour - even if you wind up with a private room by default.