Join Trek Travel for a bike tour in Oregon to see Crater Lake and the Oregon Cascades
Oregon bike tours
Ride through Crater Lake National Park on a Trek Travel bike tour
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Is there a better view than this? Trek Travel's Crater Lake & Oregon Cascades bike tours
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Crater Lake Trek Travel Cycling Vacations
Join Trek Travel for a bike tour in Oregon to see Crater Lake and the Oregon Cascades Oregon bike tours Ride through Crater Lake National Park on a Trek Travel bike tour New friends on Trek Travel's Crater Lake & Oregon Cascades bike tours 21OR_Coyle07753-2_1600x670 Is there a better view than this? Trek Travel's Crater Lake & Oregon Cascades bike tours Trek Travel named a World's Best Tour Operator by Travel+Leisure 21OR_RemoteMediaFile_6553771_0_2021_08_19_09_53_50-2_1600x670 21OR_0801_ARicciMVIMG_20210805_115824-2_1600x670 Crater Lake Trek Travel Cycling Vacations

Crater Lake & Oregon Cascades Bike Tour

Crater Lake National Park to Bend and Sisters

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—all while being fully supported on the vacation of a lifetime. Pedal past snow-capped volcanic peaks that scrape the sky as you cycle from crystal blue Crater Lake to the recreation meccas of Bend and Sisters, Oregon. Then dig deeper into this quintessential Central Oregon playground as you enjoy unique microbrews, gourmet dining, and pampering accommodations on this fantastic Oregon cycling tour! Book your trip with confidence »
Take a ride on Trek Travel's Crater Lake & Oregon Cascades bike tours
$3799 Per Person
5 Days & 4 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $3799 per person View All Details
Trip Wows
Witness the breathtaking geologic wonders of alpine lakes, canyons, and volcanic peaks by cycling the Cascade Lakes Highway and visiting stunning Smith Rock State Park
Ride along the rim of the deepest, clearest alpine lake in the country in Crater Lake National Park
Enjoy organic Northwest cuisine, complemented by Willamette Valley pinots, Bend microbrews, local cheeses, and fresh produce
Take in views of lava fields and snowcapped peaks from the Dee Wright Observatory at McKenzie Pass
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, and take in views from the rim of Crater Lake at the rustic National Park Lodge
Watch the Experience
Crater Lake & Oregon Cascades Bike Tour
Everything was my favorite. The scenery, the organization, the planning of the trip which allowed everybody regardless of biking abilities to enjoy themselves, the food, the high tech Trek bikes, and the exceptional guides who took care of absolutely everything with a smile. 
-Edward, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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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:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*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 Crater Lake bike tour! After a scenic two and half hour shuttle into Crater Lake National Park, you'll be welcomed with a delicious lunch provided by your guides. After a brief orientation, safety talk, and getting comfortably fit to your Trek bike, you’ll saddle up to begin the day’s ride along the rim road that overlooks the lake’s breathtaking blue water. (Please note that, due to ongoing construction on East Rim Drive, riding the entire loop around the Crater Lake Rim will not be possible for several years, hence the out and back route to Skell Head.) The lake is one of the deepest in the world at almost 2,000 feet and was formed about 7,700 years ago when a volcano twice as high as the current rim erupted. Experts estimate that the blast that created the lake was around 42 times more powerful than the Mt. St. Helens eruption in 1980. A wealth of viewpoints tempt you along the route, as you take in one incredible view after the next. After this stunning ride, you'll get to know one another better during a social hour and dinner in the Crater Lake Lodge dining room before retiring to your room for a well-earned rest. Please note that, while the location is unparalleled, the accommodations at Crater Lake Lodge are rustic and quite basic.

Today's Ride:

Goodbye Creek to Skell Head to Crater Lake Lodge
Approximately 35 mi | 56 km and 4,680 ft | 1,426 m

Short Option:

Goodbye Creek to Skell Head
Approximately 20 mi | 32 km and 2,870 ft | 875 m


Crater Lake Lodge

Included Meals:

Lunch | Social Hour | Dinner

With Crater Lake in the rearview mirror, you'll shuttle north for an hour and a half to begin your ride along the Cascade Lakes Scenic Highway, which traces the eastern slopes of the range and winds among 14 distinct lakes. Reflections of Three Sisters, Broken Top, and Mt. Bachelor are visible on the surfaces of the lakes—these images evoke the essence of the Cascades. Midway through the ride, take a break to enjoy lunch at Elk Lake Resort. After lunch, the road climbs over the shoulder of Mt. Bachelor and descends 3,000 feet to Bend, following the bike course of the Pole Pedal Paddle race route. Tonight, you'll toast with local brews or wine (included in the price of your trip) to a big day during dinner at Zydeco Kitchen & Cocktails, which serves southern-inspired dishes with an emphasis on locally-sourced ingredients.

Today's Ride:

Cascade Lakes Highway to Bend with hill shuttle
Approximately 53 mi | 85 km and 1,800 ft | 549 m

Short Option:

Cascade Lakes Highway to Elk Lake
Approximately 32 mi | 52 km and 1,570 ft | 479 m

Avid Option:

Cascade Lakes Highway to Bend
Approximately 64 mi | 103 km and 3,300 ft | 1,006 m


The Oxford Hotel

Included Meals:

Breakfast | Lunch | Dinner with Drinks

This morning, you'll ride deeper into the high desert before stopping for a snack break at the dramatic Smith Rock State Park. This park is well-known as a world-class climbing area and is generally regarded as the birthplace of sport climbing. Take a moment to enjoy the views and snap some photos of the Crooked River as it winds its way beneath the beautiful sheer cliffs. Then it's a short ride to the town of Terrebonne where you'll enjoy lunch at local restaurant The Pump House before continuing your ride into the pine forest of Sisters. Your hotel for the remainder of the trip is also home to one of the region's best spas, Shibui at FivePine Lodge (spa appointments should be scheduled in advance, and anyone wishing to visit the spa this afternoon will not have time to do the post-lunch ride). Whichever ride distance you choose, this stellar day is sure to be a highlight of your Oregon bike tour. This evening, you are free to explore the restaurants in downtown Sisters for a dinner of your choice.

Today's Ride:

Bend to Rainshadow Organics
Approximately 51 mi | 82 km and 1,560 ft | 476 m

Avid Option:

Bend to Sisters
Approximately 65 mi | 104 km and 2,070 ft | 690 m

Short Option

Bend to Terrebonne
Approximately 39 mi | 63 km and 1,160 ft | 354 m


FivePine Lodge and Shibui Spa

Included Meals:

Breakfast | Lunch

McKenzie Pass is a gateway between the dry and the wet sides of the Cascades, and it is perhaps the most popular road to ride in the Northwest. This morning, it just happens to be right outside your back door! The 16-mile climb is a moderate grade and tops out with stunning views of expansive lava flows and magnificent views of the Cascade peaks, including Mt. Hood. The historic Dee Wright Observatory is an impressive place to take in the scenery and celebrate your conquest of the pass, because from here the next 20 miles are almost all downhill. Cruising through increasingly dense forest, you'll arrive for lunch at a shaded campground along Lost Creek. Afterwards you may choose to shuttle back to Sisters, or tackle the pass once again from the east side for a truly epic, challenging day of climbing. This evening you will shuttle to Rainshadow Organics, where you will enjoy a true Farm to Table experience. The experience begins with a private tour of the farm, during which you will learn about the regenerative and organic agricultural practices that makes food from the Rainshadow so unique and delicious. Afterward, enjoy a multi-course meal of seasonal farm-fresh ingredients on the porch.

Today's Ride:

Sisters to Limberlost Campground
Approximately 37 mi | 60 km and 2,380 ft | 725 m

Avid Option:

Sisters to Limberlost Campground Return
Approximately 73 mi | 117 km and 6,080 ft | 1,853 m


FivePine Lodge and Shibui Spa

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

This morning offers an opportunity for a final ride to round out your Central Oregon cycling trip. Venturing through the ranchlands of the high desert, today’s miles offer 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, have a long sleep-in and take a walk through downtown Sisters to explore its unique shops, galleries, and cafes before check-out.

Today's Ride:

Indian Ford Return
Approximately 21 mi | 33 km and 520 ft | 173 m

Today's Activity:


Included Meals:



hotel image

Crater Lake Lodge

Crater Lake National Park, Oregon

Explorer Accommodation | Perched on the rim of Crater Lake, you will find no better place to take in the majestic view while relaxing with a drink on the porch than the unique and historic Crater Lake Lodge. The lodge was originally constructed in 1915 and retains much of the character from that era. The rooms are relatively small and do not have phones, televisions, or air conditioning, although the incredible scenery just outside your door more than makes up for the rustic feeling of the accommodations. Please note: This is an explorer-level property. 
hotel image

The Oxford Hotel

Bend, Oregon

Trip Advisor Traveler's Choice hotel winner Luxury Accommodation | Bend'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

FivePine Lodge and Shibui Spa

Sisters, Oregon

Trip Advisor Traveler's Choice hotel winner Luxury Accommodation | Imagine 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 FivePine 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 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 Domane SL 7

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane is the best way to enjoy the ride. Trek Bikes has launched the all-new Trek Domane and now you can ride it on our trips. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes and electronic shifting. This new bike is lighter than ever before, and carbon wheels come standard on every bike. The road-smoothing IsoSpeed technology lets you ride as long as you want with less fatigue. The bike you ride on a biking vacation matters. That is why we provide the newest and best bikes in the business. Learn More


Trek Electric-Assist Domane+ SLR 7

Take the tailwind with you and leave your limits behind on the all-new Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, Domane+ SLR 7 has everything you love in a road bike, with the extra boost to take you farther than ever before. This performance e-road bike will help you on the climbs, hang with the fast group, and venture further on your cycling vacation. So go ahead – take the long way. With Domane+ SLR 7, there’s always room for more distance, more speed, and more fun! Upgrade to the Domane+ SLR 7 on this trip for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. Please contact a Trip Consultant to check availability. Learn More


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


  • Four 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, four lunches, and three dinners
  • Two social hours of drinks and hors d'oeuvres plus one dinner with beer and wine included
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Santini cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), 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
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip
  • Entrance fees for all activities, private tours, and events


  • Upgrade your ride to the Trek Electric-Assist Domane+ SLR 7 (+$399, subject to availability)
  • 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 Santini cycling jersey to keep
  • Trek Travel water bottles 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
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • 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.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this trip, we suggest a tip for your guides between $200-$250 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or Venmo or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.
  • 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?

63 kilometers / 39 miles
317 kilometers / 197 miles
667 meters / 2,188 feet
3,335 meters / 10,940 feet
The terrain is varied with rolling hills, some sustained climbing (up to 16 miles) at relatively high elevation (up to 7,700 feet above sea level) on moderate grades (up to 9%). Our Oregon and Crater Lake bike tour is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Please be aware that some sections of the iconic rim road along the Crater Lake Rim features some sections with no shoulder and high degrees of exposure. Guests who are sensitive to heights may not find this ride to be enjoyable. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer.
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off or for 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:
  • Hike in Crater Lake National Park
  • Whitewater Raft on the Deschutes River
  • Golf in and around Bend and Sisters
  • Shop in Bend and Sisters
  • Visit spas in Bend and Sisters
  • Rock climb at Smith Rock State Park

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

Redmond Municipal Airport - Roberts Field (RDM)
8:00 AM
The Oxford Hotel, Bend, Oregon

Say Farewell

Redmond Municipal Airport - Roberts Field (RDM)
11:30 AM
The Redmond Airport (RDM) or The Oxford Hotel, Bend, Oregon


We suggest that you arrive at least one day prior to the start of your Oregon cycling tour, 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. Once you have arrived in Redmond, there are several options for getting to your pre-trip accommodations. If you wish to schedule a shuttle prior to arrival we recommend reaching out to Enviro Shuttle (www.enviroshuttle.com or 541-598-5384). Alternatively, you may call a taxi from the airport upon arrival for your transportation. Bend, where your trip begins, is located about 30 minutes south of the Redmond Airport. If you need a place to leave your personal vehicle for the week, you may valet your vehicle with the bellman at the Oxford for $25/day. Or alternatively, there is a public parking deck behind The Oxford Hotel which has a rate of $10 per day.

Your Trek Travel guides will meet you at The Oxford Hotel (10 NW Minnesota Ave, Bend) at 8:00 AM on the first day of the trip. Please arrive to the meeting location with your cycling gear packed in a day bag and separate from your main luggage. We encourage you to come dressed in your cycling clothes and comfortable walking shoes due to limited facilities in which to change at our ride start location. A two and a half hour shuttle will take you to your first destination deep in the Cascades—Crater Lake National Park. After lunch with the group, you will receive a personal bike fit to ensure a smooth and comfortable ride. Afterward, your guides will present information on safety and equipment usage along with an overview of the day’s ride. Then you’ll set out for a ride along Crater Lake’s dramatic rim.

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, Crater Lake Lodge (541-594-2255), and leave a message with your expected arrival time and contact details. There are no scheduled shuttle services offering direct access to Crater Lake, and while you may be able to hire a taxi or shuttle service, please be warned that the cost involved may be significant. We strongly recommend that you arrive the night before to ensure you do not miss our Trek Travel shuttle.

View our pre hotel recommendations


You will say farewell to your guides at 11:00 AM at Five Pine Lodge. 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 personal vehicle or extend your stay in the area, your guides can drop you off at The Oxford Hotel following 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 for an Oregon bike tour, as skies are typically crystal clear blue combined with very low humidity (10-20%). Daytime temperatures can be pleasantly temperate to quite hot (high 70s to mid 90s) with evenings dropping to the high 30s in Crater Lake National Park and the low 50s in Bend and Sisters. 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 & 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 forever! You can explore one of Central Oregon's rivers, fed by crystal-clear mountain snow, in a canoe or kayak. Into golf? Central Oregon has also 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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