My tour

Bend Breakaway



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-plus sun-drenched days each year equals nearly endless playtime! Ride the Crooked River. Visit spectacular Smith Rock, one of the most renowned rock-climbing spots in the continent. Ride up McKenzie Pass to see the volcanic minefield. Taste-test local microbrews. Spend the last night at Five Pine Lodge, voted tripAdvisor ‘top Five Hotels in the nation.’

Road bike
4 days
222 km / 138 mi
$ 2,634.-
  • Crooked River Scenic Byway
  • Smith Rock State Park
  • McKenzie Pass
  • Willamette National Forest and Deschutes National Forest.
  • Tour is suitable for all levels. Daily distances between 20 - 50 miles
  • Deposit 25%



Road bike
4 days
Easy = untrained, normal physical condition
Moderate = regular cyclist, good condition
Challenging = experienced, well trained
Guided = with cycling guide(s) - support van
Self Guided = individual - directions+maps
Daily distance
40-60 km / 25-37 mi
Total distance
222 km / 138 mi
Deluxe = 4-5 star hotel or excellent B&B
Basic = 1-2 star hotel/motel or B&B
Camping = tent, sports hall or campus
Deluxe, full board
Luggage transport
Daily luggage transfers
18 Jun 2023 - 21 Jun 2023
02 Jul 2023 - 05 Jul 2023
Airport at start
Bend Municipal Airport
Airport at finish
Bend Municipal Airport

Prices *Please note the prices are subject to change depending availability*

Price per person / please note the prices are subject to change depending availability
The tour price per person
$ 2,634.-
E-bike rental
E-bike Fastroad E+ EX Pro or E-bike THRIVE E+ EX Pro
$ 200.-
Single supplement
If you travel alone a single supplement is charged. With some group tours you can avoid a single supplement by sharing a room with another rider.
$ 711.-


Included / Not Included – lodging

Day 1: Meet in Bend. Ride 30 miles on impeccable roads from Dutchman Flat to Crane Prairie.

Bend, Oregon is an outdoor lover’s mecca. The combo of high desert climate and the 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. The 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.
Meals: Lunch and Dinner. Lodging: McMenamin’s Old St. Francis School
Distance: 29 miles (or more)
Elevation: +343 ft / – 2228 ft. (or more)

Day 2: Bicycle from Bend to Sunriver

Bike more incredible roads today through the 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 is on your own tonight in Bend; your guide will have plenty of options there.
Meals: Breakfast and Lunch. Lodging: McMenamin’s Old St. Francis School
Distance: 38 miles
Elevation: +2607 ft / – 2167 ft.

Day 3: Ride the Crooked River Scenic Byway and visit Smith Rock State Park

Ride one of Oregon’s best kept secrets today! The Crooked River Scenic Byway is a narrow, twisting basalt canyon is guaranteed to take you back in time to the Oregon Trail days of yore. This is some of the most sublime scenery in Central Oregon: spectacular views of the snow-capped Cascade mountains, rim-rock canyons, high-desert pastureland and tranquil rivers. As if that weren’t enough for one day, in the afternoon we stop off at Smith Rock. Regarded as the birthplace of U.S. sport rock-climbing, it is also one of the Seven Wonders of Oregon. After a short hike to stretch our legs, we head onward to Sisters, gateway to the equally famous McKenzie Pass. Stay tonight at the gorgeous Five Pine Lodge, one of Tripadvisor’s ‘Top Five Hotels in the Nation.’
Meals: Breakfast, Lunch and dinner. Lodging: Five Pine Lodge
Distance: 38 miles (or more)
Elevation: +1461 ft / – 1461 ft. (or more)

Day 4: Bike McKenzie Pass, which ridewithGPS calls " undoubtedly the most spectacular ride in Central Oregon"

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.
Meals: Breakfast and Lunch
Distance: 33 miles
Elevation: +2311 ft / – 2311 ft.

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.


All breakfasts and lunches, one dinner on your own.
Road / hybrid bike, E-bike rent possible
hiking & beer sampling
Luggage transfer

Not included:

Night before and after the tour.
Flights to and from the tour
Gratuities guides


McMenamin’s Old St. Francis School
Five Pine Lodge

Vaccine or test: A negative Covid test will be required within 72 hours of departure for all non-fully vaccinated guests. or Proof of a completed Covid vaccination course can be used in lieu of a Covid test. A "completed Covid vaccination course" means that the guest has had 1 or 2 shots (depending on vaccine brand) and has completed the 2-week waiting period post final shot.
All of our guides are fully vaccinated.

Map & Routes



A road or Hybrid bike is included in the price,
are available for an extra fee.
Prior to your bike tour, we request your height in order to choose the right frame size for you. (If you have a fit sheet or sizing information on your personal bicycle, you are welcome to send that to us, and we will do our best to match your geometry and specs.) On the first day of each bicycle tour, your guides tweak your bike fit to make sure you are as comfortable as possible. If they can’t get the fit just right, we typically carry a couple of extra sizes. We try to make sure we have the right size and type of bike you need to enjoy your cycling vacation.

Giant Defy ADV 3

Choose the longer route. Climb higher mountains. This all-new endurance road bike is purpose-built to help you tackle long-distance road rides in all types of conditions. It’s smooth, it’s efficient, and it’s fast.
Ride farther and faster with an all-new composite frameset that’s engineered with endurance geometry and built-in compliance. Handcrafted with Advanced-grade composite material, it’s engineered with tube shapes that are optimized to absorb road shocks and vibrations. And the frame is still stiff in all the ways that matter—for pedaling efficiency as well as steering and cornering precision. It’s made with a specific carbon layup to give it just the right feel. And for added control, it features integrated disc brakes with flat mounts and 12mm thru-axles. The D-Fuse Seatpost and handlebar system also help reduce road vibrations, adding to its smooth, compliant feel on the road.
Components: Giant Conduct disc brakes, Shimano Tiagra groupset, 50/34 cranks, 11 x 34 cassette, Giant S-R2 tubeless wheelset 700x28c

Hybrid / flat Bar Road bike

The perfect balance of road bike speed and city bike versatility. Built on a lightweight ALUXX SL aluminum frameset, this new flat-bar road bike puts the rider in a comfortable position that’s smooth and efficient. The fast-rolling 700c wheels and vibration-absorbing composite D-Fuse seatpost help smooth out rough roads. The fast-rolling 700c wheels can accommodate large tires up to 32c, perfect for tackling rough roads with confidence and control, while integrated ergo bar ends keep your hands comfortable on longer adventures. Powerful disc brakes give you added control in all types of weather, and easy-to-use rack mounts make FastRoad SL a smart choice for commuting, fitness riding and weekend adventures.
E-Bike Thrive E+ EX PRO
With THRIVE E+ EX PRO, you get an all-access pass to speed no mater what your fitness level
Designed with Liv’s 3F Design Philosophy, Thrive E+ EX Pro is the first road E-bike built specifically for women. Get up to speed fast with the new SyncDrive Pro motor that provides a natural, yet powerful, E-bike experience. The new motor also features a Smart support mode that automatically adjusts the support level based on your ride. PedalPlus 6-Sensor Technology translates six measurements about your riding and adds the perfect amount of power at just the right time for a fast and fluid ride quality. The EnergyPak Smart 375 battery is so sleek, you’ll have your friends looking twice to know it’s an E-bike.
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