Ride through lush forests of Oregon
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Mountain bike, paddle and taste your way through Bend

You may find Bend, Oregon to be more than a mountain biking destination, you just may want to call it home. Bend is synonymous with amazing beer and even better dirt. It's the perfect place to spend some time outdoors on a mountain bike tour loaded with flowy, purpose-built single track through dense forests and dramatic volcanic landscapes. Central Oregon is home to world class riding on an expansive network of hundreds of miles of trails and it's growing every year. Best of all, each post-ride reward can be found floating the crystal waters of the Deschutes and in the craft breweries that make this Oregon paradise famous.
$2999 Per Person
4 Days & 3 Nights
Rider Type: ?
3 - Active Non-riders Welcome
Hotel Style: ?
Bikes Included:
From $2999 per person View All Details
Trip Wows
Stroll the banks of the "Bend" of the Deschutes River that flows beneath the snow-capped Cascade Range and borders the Oregon high desert
Named a top city with the most eateries per capita, Bend boasts a variety of restaurants that pride themselves on using locally sourced organic meats and produce. From food-carts to fine wine, Bend has something to offer every palate!
See why Bend is dubbed Beer Town USA! Sample from any of the 22 world-class micro and craft breweries found in Bend
Visit Backporch Coffee Roasters and grasp Oregon's coffee culture on a private tour and tasting at their unique Bend roasting operation
Canoe under the brilliant Oregon night sky on one of Bend's Cascade Lakes on a nighttime canoe trip with our friends at Wanderlust
Watch the Experience
The focus of our Bend Mountain Bike Multisport Trip is not only to show you what seasoned mountain bikers refer to as some of the best trails in the entire country, but to showcase the true heart and soul of what Outside Magazine recently dubbed "The Best Multi-Sport Town" of 2017.
-Tony Ferlisi, Trip Designer

Dates & Prices

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There are currently no dates available to book for this trip or it is by request only. Please contact a Trip Consultant for more information on available dates.
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Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. All you need to do is pick any open trip date, get your group together and we will do the rest. Private trip pricing is as follows:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
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Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Upon arrival to Bend, our guides will discuss the rules of bike safety and specific mountain tips for riding throughout Bend and the surrounding area over a picnic lunch on the banks of the Deschutes River. You’ll spend some time familiarizing yourself to the Trek bikes you’ll be riding and your guides will make sure that you and your bike are the perfect fit. Please pack your bike clothes and riding equipment in a separate, easily accessible bag. Today’s ride takes you to the purpose-built Phil's Mountain Bike trails, a network of smooth, fast, winding singletrack that will offer a perfect introduction to your bike and the area. Post-ride, you’ll return to your home for the next 3 nights in downtown Bend, the Doubletree by Hilton. We'll reconvene for beers, conversation and an awesome meal together at one of Bend's most popular local gathering spots: The Lot.

Today's Ride:

Phil's trails
Approximately 23 miles with 1,600 feet of climbing


Doubletree by Hilton

Included Meals:

Lunch | Dinner

Today starts a dive right into the coffee roasting culture of Bend: a private tour of Backporch Coffee Roasters unique local roasting operation. Afterward, grab your bike and hop on a late morning shuttle up to the Wanoga Park trail complex. After a few short climbs, you will descend down one of Bend’s most iconic trails, through a network of ponderosa pine and smooth, flowy singletrack in the shadow of Mt. Bachelor. Take time this afternoon to enjoy lunch on your own downtown, and maybe hop on a different kind of trail - the Bend Ale Trail, to explore some of the 22 breweries in town. Tonight, grab a quick bite before heading up to the Cascade Lakes for a private Starlight Canoe Tour. Paddle under the brilliant Central Oregon night sky, relax and enjoy a beer or hot chocolate and take in the majesty of this amazing region.

Today's Ride:

Wanoga Complex - Tiddlywinks, Kiwa Butte, Tyler's Traverse, Funner
Approximately 18 miles with 500 feet of climbing

Short Option:

Tiddlywinks, Kiwa Butte, Tyler's Traverse, shuttle back to town
Approximately 13 miles with 500 of climbing


Doubletree by Hilton

Included Meals:


Today starts out with a morning shuttle to Swampy Snow Park nestled in the foothills of the Cascade Mountains. Your ride begins by pedaling through the dense Lodgepole pines of the Deschutes National Forest as you traverse the popular wintertime Nordic trails to sweeping volcanic vistas. A rewarding descent will bring you to the famed Upper and Lower Whoops Trails. A true "choose your own adventure trail." Stop for a trailside snack and catch glimpses of South Sister and Broken Top to the south. Finish your ride at Phil's Trail Complex and choose to pedal or shuttle back to town if you like. This afternoon, grab a stand-up paddleboard or a tube on us and float through town on a stretch of the Deschutes River or simply keep exploring the many charms of Bend. You may want to pop into McMenamins Old St Francis School, a former Catholic schoolhouse renovated into a Brewpub, theater, whiskey bar and heated, open-air soaking pool. Tonight, we'll gather for one last meal and cold micro-brew at Bend's famed Crux Fermentation Project. Spread out a few blankets on the lawn and toast the past few day's adventures and make plans for more...

Today's Ride:

Swampy Complex - Swede Ridge, Upper Whoops, Lower Whoops, Phils
Approximately 15 miles with 1,200 feet of climbing

Avid Option:

Today's ride plus riding back to town on from Phil's
Approximately 20 miles with 1,300 feet of climbing


Doubletree by Hilton

Included Meals:

Breakfast | Lunch | Dinner

This morning's ride offers a great opportunity to spin out your legs after 3 big days of mountain biking and adventuring. From the hotel, you'll shuttle to Shevlin Park, which offers a tranquil backdrop for smooth trails and a whispering breeze amongst the aspen leaves and tamarack trees. You may choose to pedal a short 5-mile loop along Shevlin Creek, or a longer out and back offering steady, gradual climbing before enjoying a speedy descent back the way you came. After riding back to the hotel, you'll say goodbye to your guides before checking out.

Today's Ride:

Shevlin Park Loop
Approximately 14 miles with 1,200 feet of climbing

Avid Option:

Mrazek out and back
Approximately 25 miles with 2,000 feet of climbing

Included Meals:



hotel image

Doubletree by Hilton

Bend, Oregon

Set in the heart of historic downtown Bend, the contemporary DoubleTree by Hilton Hotel is just steps away from numerous recreation areas, shops, restaurants and galleries, and offers incredible views of the Cascade Mountain Range, your home away from home for 4 nights.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Fuel Ex 9 29

The world’s best-loved mountain bike keeps getting better. This is the perfect trail bike. Fuel EX continues to set the bar for full suspension trail bike versatility, bringing race-day tech to all-day adventure. Whether it’s your millionth mile on the trail or your first, you’ll love this bike. Learn More


  • 3 nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, 2 lunches and 2 dinners
  • 1 social hour of drinks and hors d'oeuvres
  • Ride a Trek Fuel EX 9 full suspension mountain bike
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless mountain pedals
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized photobook of your trip
  • Entrance fees for all activities, private tours and events


  • Trek Fuel EX 9 full suspension mountain bike
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless mountain pedals
  • Bontrager helmet and saddle
  • Flat pack
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email.
  • Please be sure to bring a Camelback, or similar hydration pack with pockets to carry additional items needed on the trail. Limited vehicle support means you will want to carry an extra layer, multi-tools, food and water.
  • You may bring your own pedals and saddle on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

18 miles
70 miles
900 feet
4,500 feet
The terrain is of the singletrack in and around Bend is smooth and flowy, lending itself to covering miles quickly, however there is varied terrain offering sections of technical and rocky singletrack. Daily rides during the Bend Mountain Bike trip range from 11 to 40 miles in forrested, high-desert and mountainous regions between the elevations of 3,000 and 6,000 feet. While there are many challenging mountain bike options, there will always be more moderate options available for novice mountain bikers. Bend Mountain Bike is best suited for our Type 3 Riders with at least intermediate technical mountain biking skills. Those who want more miles and more technical terrain and those who want less may split into two groups in order to ride different trails or simply go at different speeds. If you choose not to ride with a guide you will need a thorough understanding of the trail map, adequate food and water, and tools to address bike repair issues that may arise. Cell coverage is limited in the areas you’ll be riding so you must be self-sufficient. We will offer shuttles to and from the trailhead some days, but other rides begin and end closer to town, or in town. You are always welcome to ride directly back to the hotel for more miles on the days that shuttles are offered. Each day, depending on the featured ride, the weather, and the desires of the group, your guides will decide how best to support the ride with a combination of on the bike support and vehicle support.
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options on this trip are:
  • Check out the shops of Bend
  • Soak in the thermal baths at McMenamins
  • Standup paddleboard, kayak, canoe, float or raft on the Deschutes River
  • Starlight canoe trip on one of the Cascade Lakes
  • Backporch Coffee Roasters Tour and Tasting
  • Hike the nearby mountains and trails
  • Enjoy a brewery tour at Deschutes Brewery
  • Indulge yourself with a spa treatment at Anjou or Spa W

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

Redmond Airport (RDM)
11:00 AM
Doubletree by Hilton, Bend, Oregon

Say Farewell

Redmond Airport (RDM)
1:00 PM
Doubletree by Hilton, Bend, Oregon


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Redmond (RDM). All major car rental companies are available at RDM or Shuttles and taxis are available from Redmond to Bend for approximately $35. Enviro Shuttle offers ride share rates based on availability, or a door to door service for $30. Visit Enviro Shuttle for more details. Alternatively, Checker Cab offers door to door service for $35. Visit Checker Cab or call (541) 390-0962.

Trek Travel staff will meet you at the The Doubletree by Hilton (300 NW Franklin Avenue, Bend, Oregon 97701) at 11:00 AM on the first day of your trip. Please have riding gear and clothes for the first day easily accessible and separate from your luggage. Your guides will walk you through town to a park for a quick bite to eat, followed by a mountain bike fitting. The guides will brief you on the activities for the day before you set out for the trails.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Doubletree by Hilton (541-317-9292), and leave a message with your expected arrival time and contact details. You can make arrangements with a number of taxi companies or shuttles from the Redmond Airport. RDM is approximately 20 minutes from Bend so transport is quite easy. Please refer the Redmond airport website for options: Redmond Airport Ground Transportation

View our pre hotel recommendations


You will say farewell to your guides at the Doubletree Hotel at 1:00 PM. Please coordinate transportation from the hotel to the Redmond Airport for your departure.

The use of your Trek Travel bike ends at 12:00 PM on day of departure. Extensions may be available upon request but cannot be guaranteed before your trip begins.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Bend enjoys the predominately dry climate of the high desert with an average of almost 300 days of sunshine per year. Sunny days, low humidity, and cool nights provide the most common weather pattern for the area. Summer temps average between 60F and 85F degrees for the high (depending on elevation of rides) with average lows in the mid 40's F. Packing List

Before and After Your Trip


Before & After: Bend, Oregon

Bend is an outdoor lovers dream. With so many things to do you may just want to stay here! You absolutely have to tackle one of Central Oregon's rivers fed by crystal-clear mountain snow in a canoe or kayak. Into Golf? Central Oregon has been rated as one of the top 50 golf destinations in the world! Don't forget about the fishing and hiking opportunities too.

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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