Oregon's Cascades & Crater Lake Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

From $3,899 - $4,249 /person

6 days

5 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

Oregon's Cascades & Crater Lake Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

6 days

5 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

2024: Jun-Sep 2025: Jun-Sep

From $3,899 - $4,249 /person

Bend, Three Sisters & the Deschutes River

Now this is living! Sun shining. Legs pumping. It’s official, you’re in love. With the rugged beauty along the mighty Deschutes River. The laid-back, small-town feel of friendly Bend. And the stunning Cascades. You’re sure life can’t get any better. Then you kick back on the deck of the lodge and find yourself mesmerized by the indescribable blue hues of Crater Lake. And excited for what's in store for you tomorrow on our Oregon bike tour.

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Highlights

  • Embark on challenging and exhilarating routes amid magnificent scenery in rugged Central Oregon's high country 
  • Bike McKenzie Pass, one of the most spectacular rides in the Pacific Northwest, showcasing stunning views of the Cascades 
  • Explore Bend, a former mill town turned adventure playground with more breweries per capita than anywhere in Oregon 
  • Skirt the rim of Crater Lake's world-famous caldera—one of Bicycling magazine's favorite rides—for breathtaking vistas
Oregon Cascades & Crater Lake Bike Tour map

Oregon

Start/End Bend

Airports & Travel details*

* Start/End locations may vary. Do not book flights until your trip details are confirmed.

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Itinerary

Days 1-2

Description

Explore Smith Rock State Park—a playscape for outdoor enthusiasts—on foot before heading out on a bike ride through fertile ranchland along a portion of the Oregon Scenic Bikeway • Savor a picnic lunch along the shores of the mighty Deschutes River • Check out the Old West-style town of Sisters, perhaps stopping for a post-ride pint at a local craft brewery • Western hospitality and plush amenities await at FivePine Lodge • ​Our welcome reception and dinner at a favorite family farm is the perfect ending to our first day in Oregon • Pedal McKenzie Pass, one of the Pacific Northwest's most beautiful cycling routes, past ancient lava flows and into a lush valley • Treat deserving muscles to a riverside hot-spring soak.

Accommodations
FivePine Lodge

(2 nights)

Nights 1-2

FivePine Lodge
Sisters
Premiere Hotel

Soak up the elegant Western-style ambience at this lodge, nestled in beautiful surroundings and featuring a brewpub, athletic club and even a movie house. (pool, spa)  

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 3-4

Description

Pedal along smooth roads on the scenic outskirts of Bend with grand views of the Cascades in the distance • Explore Bend, Oregon's vibrant adventure capital • Thirsty? Cruise downtown to find out what's on tap at over 20 local craft breweries • Experience the alpine splendor of Mount Bachelor as you bike a route from Elk Lake that ends with a thrilling descent back into town • Maybe you'll choose to join your leaders on a private tour of a famous local brewery • Bend's culinary scene offers plenty of enticing options for dinner on your own.

Accommodations

Nights 3-4

The Oxford Hotel
Bend
Premiere Hotel

A luxury boutique hotel ideally located amid the shops, galleries, cafés and brewpubs of vibrant downtown Bend. 

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 5-6

Description

Welcome to Crater Lake National Park—ready to bike the iconic Rim Drive? • As you circle this enormous caldera on two wheels, admire the lake's intense sapphire color and amazing clarity • Each curve in the road brings another incredible vista, from the cinder cone of Wizard Island to the 9,000-foot peak of Mount Scott • Unwind at the lodge or explore the spectacular landscape on foot • Hike up Garfield Peak for a stunning bird's-eye-view of the lake and its surrounds.  

Accommodations

Night 5

Crater Lake Lodge
Crater Lake National Park
*Casual Hotel

Perched on the crater's rim, this classic national park lodge transports you to a bygone era.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

What's Included

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Straight Talk

We want to make sure you're on the trip that's right for you. Every Backroads trip is unique and this one is no exception.

Accommodations

Crater Lake Lodge is a historic national park property offering simpler accommodations than typical Backroads lodging. It has been selected for its stunning location on the rim of Crater Lake, and its access to world-class riding. Although clean and comfortable, the guest rooms are basic and not equipped with televisions or air-conditioning (nights are usually cool due to the high elevation). Generally speaking, service can seem slow and casual in national parks when compared with the high standards of hospitality found on other Backroads trips.

Want more information? Download a detailed itinerary.

Itineraries include detailed descriptions of each day, tips on travel arrangements, regional highlights and more. It's the perfect tool to help you choose!

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From $3,899 - $4,249 /person

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Hotels

World-Class Hotels

Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Nights 1-2

FivePine Lodge
Sisters

Premiere Hotel

Soak up the elegant Western-style ambience at this lodge, nestled in beautiful surroundings and featuring a brewpub, athletic club and even a movie house. (pool, spa)  

Nights 3-4

The Oxford Hotel
Bend

Premiere Hotel

A luxury boutique hotel ideally located amid the shops, galleries, cafés and brewpubs of vibrant downtown Bend. 

Night 5

Crater Lake Lodge
Crater Lake National Park

*Casual Hotel

Perched on the crater's rim, this classic national park lodge transports you to a bygone era.

From $3,899 - $4,249 /person

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Bikes

Choose Your Perfect Bike

Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Backroads Performance Racer 2.0
Backroads Next Generation Performance Road Bike

Included in your trip price

  • Ideal for avid cyclists
  • Redesigned for 2024
  • Next gen titanium frame with carbon wheels
  • Responsive, efficient and comfortable
  • Drop handlebars only
Backroads Touring Bike
Backroads Touring Bike

Included in your trip price

  • Suited for a wide range of cyclists
  • Comfortable ergonomic seat
  • Long wheel base adds to the bike's control and stability
  • Upright handlebars only
Backroads Electric-Assist Bike
Backroads Electric-Assist Bike

Included in your trip price

  • One of the lightest e-bikes available
  • Provides plenty of power and more than enough battery
  • Lower top tubes for easier mounting and dismounting
  • Upright handlebars only

Min. age to ride e-bike: 16+

Canyon Endurace SLX 9 Di2
Canyon Endurace SLX 9 Di2
  • $650 rental fee; subject to availability
  • Ride like a pro with the top-of-the-line carbon Canyon Endurace CF SLX 9 Di2
  • Perfectly balanced comfort and performance with a Grand Tour pedigree
  • State-of-the-art components and precision German engineering
Co-Motion Torpedo Tandem Bike
Tandem Bike
  • $400 rental fee
  • Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
  • Custom upgraded wheelset
  • Best for riders with some tandem experience.

From $3,899 - $4,249 /person

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From $3,899 - $4,249 /person

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Dates & Prices

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Want more information? Download a detailed itinerary.

Itineraries include detailed descriptions of each day, tips on travel arrangements, regional highlights and more. It's the perfect tool to help you choose!

Request itinerary

Book with Confidence

Backroads provides flexible booking policies so that you can plan your vacation with complete peace of mind.

Learn more

From $3,899 - $4,249 /person

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