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ORSG - Mt Bachelor - Canva ©16OR0724_zjones-2917-1600x670 ORSG - Smith Rock State Park - Canva crater-lake-oregon-cascades-05-1600x670 19OR0825_JAKER_19OR0825_JAKER_IMG_2172 - 1600x670 crater-lake-oregon-cascades-04-1600x670 Crater Lake and Oregon Cascades-223 13or0728_zjones_1600x670

Oregon Cascades Self-Guided Bike Tour

Bend to Sisters, the best of the Oregon Cascades

To immerse yourself in the drama, nuance, and wonder of the Oregon Cascades on two wheels is to experience one of the world’s most dynamic landscapes. On our Oregon self-guided bike tour, pedal beneath towering snow-capped volcanic peaks and past crystal blue alpine lakes to the recreation meccas of Bend and Sisters. Dig deep into this quintessential central Oregon playground with options to enjoy whitewater rafting, a lava cave tour, or numerous other adventures coupled with unique craft brews, contemporary gourmet dining, and pampering accommodations on this self-guided bicycling vacation!Learn if a self-guided trip is right for you »
From:
$2799 Per Person
Duration:
5 Days & 4 Nights
Rider Type: ?
3 - Active Non-riders Welcome
From $2799 per person View All Details
Trip Wows
Witness the breathtaking geologic wonders of alpine lakes, canyons, and volcanic peaks while cycling the Cascade Lakes Highway and visiting stunning Smith Rock State Park
Savor organic Northwest cuisine, complemented by Willamette Valley pinots, Bend craft brews, local cheeses, and heirloom produce
Explore the outdoor activity mecca of Bend with the option to go whitewater rafting on the Deschutes River, explore a lava cave with a naturalist, take a relaxed paddling trip, or go on a brewery tour
Relax and enjoy the dreamy, freewheeling culture that makes central Oregon a great place to visit as you stay in top-rated properties in Bend and Sisters
Enjoy riding at your own pace on quiet mountain and high desert roads and pick the level of challenge that is right for you with multiple daily riding options
Watch the Experience
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
-John, Trek Travel Guest

Dates & Prices

Early Booking Savings Ends October 7th

Book today for the best savings of the year and the widest availability of dates. Not sure where or when you want to travel?
We don’t charge a fee for changing dates or destinations up to 90 days prior to your trip start.
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Available in 2020 and 2021. Our trip on your schedule. Simply choose your own travel dates and we will handle the rest. Price may vary based on hotel availability and dates requested. Contact our Trip Consultants today at 866-464-8735 to get started.
Don't see your ideal travel date? 
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. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 Departure Dates:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*


2021 Departure Dates:
  • 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 +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*
*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.
Looking for a date that you don’t see?
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.

Welcome to the first day of your self-guided Oregon bike tour! Your guide will meet you at 8:00 AM in the lobby of The Oxford Hotel in downtown Bend. Please arrive dressed in your cycling clothes and bring along anything you will need for the day’s ride. You are free to bring along a daybag for the first portion of the day, as your guide can drop this off for you at the hotel after lunch (the remainder of your luggage will be stored at the hotel until check-in). After meeting your guide, you will walk a short distance for a coffee and a brief orientation. Here your guide will make sure you are fitted comfortably on your bike and will share some safety tips. You will then shuttle approximately 50 minutes to the Crane Prairie Reservoir, where you'll saddle up to begin the day's ride along the Cascade Lakes Scenic Highway. Your route traces the eastern slopes of the range along numerous lakes and peaks, where reflections of the Three Sisters, Broken Top, and Mt. Bachelor are visible on the surfaces of the lakes—these images evoke the essence of the Cascades. Partway through the ride, take a break to enjoy lunch on Trek Travel with your guide at Elk Lake Resort. From Elk Lake, the road climbs over the shoulder of Mt. Bachelor and gradually descends 3,000 feet over the next 21 miles to Bend and your home for the next two nights at the Oxford Hotel. Settle in and enjoy dinner on us at the hotel’s restaurant, 10 Below.

Today's Ride:

Cascade Lakes Highway: Crane Prairie to Bend
Approximately 44 miles with 2,440 feet of climbing

Short Option:

Cascade Lakes Highway: Elk Lake to Bend
Approximately 32 miles with 1,830 feet of climbing

Hotel:

The Oxford Hotel

Included Meals:

Lunch | Dinner

Following breakfast at 10 Below, begin your day with a brief morning ride on a beautiful road that climbs into the Tumalo Creek watershed. If you like, you may tack on an extra 5 miles on a gravel road to visit the 97 foot-tall Tumalo Falls. This afternoon is an opportunity to enjoy an adventure with one of our partners (included in the price of your trip). Choose from rafting, exploring a lava tube with a naturalist, kayaking or canoeing on one of the Cascade lakes, or touring a selection of the craft breweries and distilleries (you will be asked to select your activity at the time of booking). You can also opt to have your own adventure by renting mountain bikes and riding the world-class Phil's Trail system, hiking the Deschutes River Trail, floating the river near town, playing golf at one of the many area courses, or getting a massage or spa treatment. The choices are almost endless, and we have hand-selected the best of Bend for you to explore on your own. Those interested in more riding instead of an off-the-bike experience can continue the morning ride by adding on the High Desert Loop, which offers rolling hills on rural roads and panoramic views of the Cascade range. Also, be sure to take some time today to relax in the Oxford's hot tub, sauna, or steam room, located on the 7th floor of the hotel. Tonight is yours to explore downtown on your own and check out one of the many eclectic and delicious eateries.

Today's Ride:

Tumalo Creek Return
Approximately 22 miles with 1,350 feet of climbing

Today's Activity

Whitewater Rafting, Brewery Tour, Paddling Trip, or Lava Tube Exploration

Avid Option:

Tumalo Creek Return with High Desert Loop
Approximately 53 miles with 2,820 feet of climbing

Hotel:

The Oxford Hotel

Included Meals:

Breakfast

This morning, you'll ride out into the high desert before heading into the cooler Ponderosa Pine forests of Sisters. While you are out on your ride, your luggage will be transferred to your next hotel and you will find it already in your room upon arrival. Today's riding option heads north for a visit to the dramatic Smith Rock State Park. This park is well-known as a world-class climbing area and is regarded as the birthplace of sport climbing. Take some time to enjoy the views and snap some photos of the Crooked River as it winds its way beneath the beautiful sheer volcanic tuff cliffs. Stop for lunch in Terrebonne before continuing along at your own pace down quiet country roads into the pine forest of Sisters. The short option takes you northwest through ranches and forests, skipping Smith Rock to bring you more directly to Sisters in half the mileage of the basic option. Your hotel for the remainder of the trip is home to one of the region's best spas, Shibui at Five Pine Lodge (spa appointments should be scheduled in advance, and anyone wishing to visit the spa this afternoon will need to plan ride time accordingly). Whichever ride distance you choose, this stellar day is sure to be a highlight of your Central Oregon cycling vacation. This evening, check out one of our recommended restaurants in the quaint town of Sisters.

Today's Ride:

Bend to Sisters via Smith Rock
Approximately 65 miles with 2,070 feet of climbing

Short Option:

Bend to Sisters Direct
Approximately 29 miles with 970 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

McKenzie Pass is a gateway between the dry and the wet sides of the Cascades and is perhaps the most famous road to ride in the Northwest. This morning, it just happens to be right outside your back door! The 16-mile climb out of Sisters is a moderate grade and tops out amidst an expansive lava flow with magnificent views of the Cascade peaks, including Mt. Hood. The historic Dee Wright Observatory is an impressive location to take in the scenery and celebrate your conquest of the pass. Then, the 16-mile descent back to Sisters awaits. Grab lunch of your choosing in Sisters then you may head out on one of the afternoon add on routes for more miles. Alternatively, you may decide to strike out on a hike or rent a mountain bike from Five Pine Lodge to explore the Peterson Ridge trails just out your backdoor. This evening you will choose another of Sister's charming eateries to celebrate the final night of your cycling getaway.

Today's Ride:

Sisters to McKenzie Pass Return
Approximately 32 miles with 2,300 feet of climbing

Afternoon Add On Options:

Holmes Road Loop or Three Creeks Return
Approximately 38 miles with 1,120 feet of climbing or 23 miles with 1,970 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

This morning offers an opportunity for a final ride to round out your self-guided bike tour in Oregon. Venturing through the ranchlands of the high desert, today’s 21 miles provide the chance to take one more deep breath of rejuvenating sage-soaked air and snap any final photos of the Cascades before moving on to your next adventure. Alternatively, sleep in and take a walk through downtown Sisters to explore its unique shops, galleries, and cafes before checkout.

Today's Ride:

Indian Ford Return
Approximately 21 miles with 520 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

Welcome to the first day of your self-guided Oregon bike tour! Your guide will meet you at 8:00 AM in the lobby of The Oxford Hotel in downtown Bend. Please arrive dressed in your cycling clothes and bring along anything you will need for the day’s ride. You are free to bring along a daybag for the first portion of the day, as your guide can drop this off for you at the hotel after lunch (the remainder of your luggage will be stored at the hotel until check-in). After meeting your guide, you will walk a short distance for a coffee and a brief orientation. Here your guide will make sure you are fitted comfortably on your bike and will share some safety tips. You will then shuttle approximately 50 minutes to the Crane Prairie Reservoir, where you'll saddle up to begin the day's ride along the Cascade Lakes Scenic Highway. Your route traces the eastern slopes of the range along numerous lakes and peaks, where reflections of the Three Sisters, Broken Top, and Mt. Bachelor are visible on the surfaces of the lakes—these images evoke the essence of the Cascades. Partway through the ride, take a break to enjoy lunch on Trek Travel with your guide at Elk Lake Resort. From Elk Lake, the road climbs over the shoulder of Mt. Bachelor and gradually descends 3,000 feet over the next 21 miles to Bend and your home for the next two nights at the Oxford Hotel. Settle in and enjoy dinner on us at the hotel’s restaurant, 10 Below.

Today's Ride:

Cascade Lakes Highway: Crane Prairie to Bend
Approximately 44 miles with 2,440 feet of climbing

Short Option:

Cascade Lakes Highway: Elk Lake to Bend
Approximately 32 miles with 1,830 feet of climbing

Hotel:

The Oxford Hotel

Included Meals:

Lunch | Dinner

Following breakfast at 10 Below, begin your day with a brief morning ride on a beautiful road that climbs into the Tumalo Creek watershed. If you like, you may tack on an extra 5 miles on a gravel road to visit the 97 foot-tall Tumalo Falls. This afternoon is an opportunity to enjoy an adventure with one of our partners (included in the price of your trip). Choose from rafting, exploring a lava tube with a naturalist, kayaking or canoeing on one of the Cascade lakes, or touring a selection of the craft breweries and distilleries (you will be asked to select your activity at the time of booking). You can also opt to have your own adventure by renting mountain bikes and riding the world-class Phil's Trail system, hiking the Deschutes River Trail, floating the river near town, playing golf at one of the many area courses, or getting a massage or spa treatment. The choices are almost endless, and we have hand-selected the best of Bend for you to explore on your own. Those interested in more riding instead of an off-the-bike experience can continue the morning ride by adding on the High Desert Loop, which offers rolling hills on rural roads and panoramic views of the Cascade range. Also, be sure to take some time today to relax in the Oxford's hot tub, sauna, or steam room, located on the 7th floor of the hotel. Tonight is yours to explore downtown on your own and check out one of the many eclectic and delicious eateries.

Today's Ride:

Tumalo Creek Return
Approximately 22 miles with 1,350 feet of climbing

Today's Activity

Whitewater Rafting, Brewery Tour, Paddling Trip, or Lava Tube Exploration

Avid Option:

Tumalo Creek Return with High Desert Loop
Approximately 53 miles with 2,820 feet of climbing

Hotel:

The Oxford Hotel

Included Meals:

Breakfast

This morning, you'll ride out into the high desert before heading into the cooler Ponderosa Pine forests of Sisters. While you are out on your ride, your luggage will be transferred to your next hotel and you will find it already in your room upon arrival. Today's riding option heads north for a visit to the dramatic Smith Rock State Park. This park is well-known as a world-class climbing area and is regarded as the birthplace of sport climbing. Take some time to enjoy the views and snap some photos of the Crooked River as it winds its way beneath the beautiful sheer volcanic tuff cliffs. Stop for lunch in Terrebonne before continuing along at your own pace down quiet country roads into the pine forest of Sisters. The short option takes you northwest through ranches and forests, skipping Smith Rock to bring you more directly to Sisters in half the mileage of the basic option. Your hotel for the remainder of the trip is home to one of the region's best spas, Shibui at Five Pine Lodge (spa appointments should be scheduled in advance, and anyone wishing to visit the spa this afternoon will need to plan ride time accordingly). Whichever ride distance you choose, this stellar day is sure to be a highlight of your Central Oregon cycling vacation. This evening, check out one of our recommended restaurants in the quaint town of Sisters.

Today's Ride:

Bend to Sisters via Smith Rock
Approximately 65 miles with 2,070 feet of climbing

Short Option:

Bend to Sisters Direct
Approximately 29 miles with 970 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

McKenzie Pass is a gateway between the dry and the wet sides of the Cascades and is perhaps the most famous road to ride in the Northwest. This morning, it just happens to be right outside your back door! The 16-mile climb out of Sisters is a moderate grade and tops out amidst an expansive lava flow with magnificent views of the Cascade peaks, including Mt. Hood. The historic Dee Wright Observatory is an impressive location to take in the scenery and celebrate your conquest of the pass. Then, the 16-mile descent back to Sisters awaits. Grab lunch of your choosing in Sisters then you may head out on one of the afternoon add on routes for more miles. Alternatively, you may decide to strike out on a hike or rent a mountain bike from Five Pine Lodge to explore the Peterson Ridge trails just out your backdoor. This evening you will choose another of Sister's charming eateries to celebrate the final night of your cycling getaway.

Today's Ride:

Sisters to McKenzie Pass Return
Approximately 32 miles with 2,300 feet of climbing

Afternoon Add On Options:

Holmes Road Loop or Three Creeks Return
Approximately 38 miles with 1,120 feet of climbing or 23 miles with 1,970 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

This morning offers an opportunity for a final ride to round out your self-guided bike tour in Oregon. Venturing through the ranchlands of the high desert, today’s 21 miles provide the chance to take one more deep breath of rejuvenating sage-soaked air and snap any final photos of the Cascades before moving on to your next adventure. Alternatively, sleep in and take a walk through downtown Sisters to explore its unique shops, galleries, and cafes before checkout.

Today's Ride:

Indian Ford Return
Approximately 21 miles with 520 feet of climbing

Hotel:

Five Pine Lodge and Shibui Spa

Included Meals:

Breakfast

Hotels

hotel image

The Oxford Hotel

Bend, Oregon

Trip Advisor Traveler's Choice hotel winnerBend's "eco-chic" boutique hotel is the pinnacle of luxury and sustainability. Fusing Northwest-inspired, modern design, world-class service, and earth-friendly practices and products, the Oxford is a perfect match for the active and cosmopolitan vibe that is Bend, Oregon. Located in the heart of downtown, shopping, dining, galleries, and a variety of activities are just a few steps or a cruiser ride away (provided with your stay). Amenities like the sauna and steam room, spa, full-service bar, and restaurant make it the perfect home for your time in Bend.
hotel image

Five Pine Lodge and Shibui Spa

Sisters, Oregon

Trip Advisor Traveler's Choice hotel winnerImagine elegant and spacious contemporary Craftsman-style cabins and lodge rooms combined with a full-service Japanese spa, all hidden in a pine forest at the base of three extinct volcanic peaks. You have just begun to picture the Five Pine Lodge. This is more than a lodge—it is a true mountain retreat from which you will not want to leave—complete with swimming pool, first-run movie theater, nightly wine and beer reception, brew pub, and a trail network for hiking right out the back door.

What's Included

For us, the details matter most

Every moment of a Trek Travel self-guided 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.

bike

Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More

bike

Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More

WHAT'S INCLUDED

  • Four nights of accommodation at handpicked hotels
  • Daily breakfast
  • One Lunch
  • One Dinner
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel Bontrager cycling jersey to keep
  • A Trek Travel water bottle to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals)
  • Bontrager WaveCel helmets
  • Transfers by private shuttle on the first and last day of the trip
  • All luggage transfers and transportation during your trip
  • A carrying case complete with a bike lock, flat kit, frame pump, all necessary accessories and chargers, spare parts and tools
  • Nutrition bars and electrolyte tablets
  • Personal bike fit by a certified guide
  • Ride With GPS app on your phone to access your daily routes and get all the information you need to travel unsupported
  • Optional daily phone or video call with the guide to prep you for the next day’s adventure
  • Recommended restaurant options in each town
  • Support on the ground in case of emergency

GEAR

  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel Bontrager cycling jersey to keep
  • A Trek Travel water bottle to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

Gratuities for your Trek Travel guide are not included in your trip price. We recommend tipping 7.5-10% of your trip price, preferably in the local currency. Please tip your guide at your discretion, based on his or her 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
  • While we provide daily breakfast, one lunch, and one dinner, other meals are not included. On self-guided bike tours, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

AVERAGE DAILY MILEAGE:
37 miles
TOTAL MILES:
184 miles
AVERAGE DAILY ELEVATION:
1,736 feet
TOTAL ELEVATION:
8,680 feet
TERRAIN: HILLY
The terrain on our Oregon self-guided bike tour is varied with sustained ascents and somewhat challenging climbs if you opt for the more difficult routes. Oregon is best suited for our Type 3 Riders. Type 4 Riders will enjoy the extra mileage the avid route options offer. Type 2 Riders, with proper bike handling skills, might find the hills challenging but could be comfortable with the climbs and mileage by opting for an electric-assist bike.
NON-RIDING ACTIVITIES:
There are a variety of non-riding options on this trip 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. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
  • Whitewater raft or float the Deschutes River
  • Golf in and around Bend and Sisters
  • Hike through Ponderosa forests
  • Go caving in a lava tube
  • Flat water paddling in a canoe or kayak
  • Shop in Bend and Sisters
  • Visit spas in Bend and Sisters

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks 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

FLY INTO:
Redmond Municipal Airport - Roberts Field (RDM)
MEETING TIME:
8:00 AM
MEETING LOCATION:
The Oxford Hotel, Bend, Oregon

Say Farewell

FLY OUT OF:
Redmond Municipal Airport - Roberts Field (RDM)
DEPARTING TIME:
11:30 AM
DEPARTING LOCATION:
The Redmond Airport (RDM) or The Oxford Hotel, Redmond or Bend, Oregon

Arriving

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 Municipal Airport - Roberts Field (RDM) in Redmond, Oregon. This airport is served by Alaska Air, American Airlines, Delta Airlines, United/United Express and Allegiant. Once you have arrived in Redmond there are several options for getting to your pre-trip accommodations. If you choose to stay at The Oxford Hotel in Bend, where you will meet your guides on the first day of your trip, the hotel offers a shuttle service for $45 each way from the airport to the hotel. Please call the hotel to schedule this service. Alternatively, you may call a taxi from the airport upon arrival for your transportation to Bend, which is located about 30 minutes south of the Redmond Airport. If you need a place to leave your personal vehicle for the week, there is a public parking deck behind The Oxford Hotel with a daily rate of $10 per 12 hours. You will need to download the local app in order to pay for parking in this public lot. Or alternatively, you may valet your vehicle with the bellman at the Oxford for $15/day.

Your Trek Travel guide will meet you at The Oxford Hotel (10 NW Minnesota Ave, Bend) at 8:00 AM on the first day of the trip. Please meet your guide prepared to ride and bring anything you need for your bike, including personal pedals, saddles, GPS units, etc. You are free to bring along a daybag for the first portion of the day, as you guide can drop this off for you at the hotel after lunch (the remainder of your luggage will be stored at the hotel until check-in). After meeting your guide, you will walk a short distance for a coffee and a brief orientation. Here your guide will make sure you are fitted comfortably on your bike and will share some safety tips. You will then shuttle approximately 50 minutes to the Crane Prairie Reservoir, where you'll saddle up to begin the day's ride. If you will be late for the pick-up or are going to miss it altogether, please inform your guide. You will receive an email a week before the trip start with his or her name and contact details. If you cannot reach them, please call our first hotel, The Oxford Hotel (+1 541-382-8436), and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations

Leaving

Your Trek Travel guide will meet you at 11:00 AM at the Five Pine Lodge to take your bike and equipment. You will then shuttle 30 minutes to Redmond, arriving around 11:30 AM at the Redmond Airport. Please allow adequate connection time for flights or other travel to accommodate possible traffic delays. If you wish to return to downtown Bend to retrieve your vehicle or extend your stay in the area, your guide can drop you off at The Oxford Hotel following or instead of the airport drop. It is about 30 minutes from the Redmond Airport to downtown Bend.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Summer is the best time to visit central Oregon, as skies are typically crystal clear blue combined with very low humidity (10-20%). Daytime temperatures can be pleasantly temperate to quite hot (high 70's to mid 90's) with evenings dropping to the low 50's. Rain is fairly infrequent, but it's always good to be prepared for the occasional thunderstorm just in case. Packing List

Before and After Your Trip

before

Before & After: Bend, Oregon

The city of Bend is well known as a mecca for lovers of all things outdoors. The vibrant downtown and Old Mill District are also great spots for eclectic dining experiences, people-watching, shopping, and local beer-tasting. With so many things to do, you may just want to stay here! You can explore one of Central Oregon's rivers, fed by crystal-clear mountain snow, in a canoe or kayak. Interested in golf? Central Oregon has been rated as one of the top 50 golf destinations in the world! Don't forget about the fishing, hiking, and mountain biking opportunities too. We recommend the following accommodations for your pre- and post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

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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