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 Teens & 20s Best for ages 16-23 (min. age 14)

Families with Kids & Teens Best for ages 7-17 (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 - Experience the world’s best, from lavish luxury to chic retreats with prestigious alliances.

Deluxe Hotels - Find modern comforts in extraordinary settings, with great ambience and ample amenities.

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 Teens & 20s Best for ages 16-23 (min. age 14)

Families with Kids & Teens Best for ages 7-17 (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 - Experience the world’s best, from lavish luxury to chic retreats with prestigious alliances.

Deluxe Hotels - Find modern comforts in extraordinary settings, with great ambience and ample amenities.

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.

2025: Jun-Sep

Bend, Three Sisters & the Deschutes River

Sun shining. Legs pumping. It’s official, you’re in love. With the rugged beauty along the mighty Deschutes River and the stunning Cascades. With laid-back, friendly Bend. You kick back on the deck of the lodge and find yourself enchanted by the indescribable blue hues of Crater Lake. And you realize you may have found your happily ever after on a bicycle in Oregon.

... Read more

Highlights

  • Embark on challenging and exhilarating routes amid magnificent scenery in rugged Central Oregon's high country 
  • Bike McKenzie Pass, enjoying stunning views of the Cascades en route to relaxing hot springs—it’s one of the most spectacular rides in the Pacific Northwest! 
  • 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
  • Read More
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

Wide shot of Smith Rock State Park.

Days 1-2

Description

Explore Smith Rock State Park 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 shore of the mighty Deschutes River • Discover the Old West town of Sisters—and perhaps a post-ride pint at a local craft brewery • Western hospitality and plush amenities await at FivePine Lodge • ​A favorite family farm hosts our welcome reception and dinner • Pedal McKenzie Pass past ancient lava flows and into a lush valley • Treat yourself 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.
Shot of flowing river among mossy forest.

Days 3-4

Description

Pedal along smooth roads on the scenic outskirts of Bend with grand views of the Cascades in the distance â€¢ 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.
Guest cycling and gesturing towards Crater Lake on her right.

Days 5-6

Description

Welcome to Crater Lake National Park—ready to experience the iconic Rim Drive? • As you bike along the edge of this enormous caldera, 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 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 simple yet classic national park lodge offers incredible view of its namesake.

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

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

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What's Included

See more

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.

From $4,099 /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 simple yet classic national park lodge offers incredible view of its namesake.

From $4,099 /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.

Bike with drop handlebars and a "New" label on the top left
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
  • Limited availability on Unplugged Bike Tours;  learn more

Min. age to ride e-bike: 16+

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 $4,099 /person

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Reviewed by 28 customers

Another fabulous Backroads adventure

Submitted July 2024

By david

From Destin, Florida

Once again, Backroads provided a great trip in a beautiful area with awesome team leaders. Leni and Jasmine were top notch in every way, and they exemplified the Backroads culture of professional, kind, smiling service! We are already looking for our next adventure.

Bottom Line Yes, I would recommend to a friend

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First biking trip & I am hooked for life! Amazing experienc!

Submitted August 2023

By susan

From Bend Oregon

Amazing first trip to Oregon & first biking excursion like this. The food, the trails, the people were just outstanding! I learned so much, got such great exercise, and laughed like crazy too!

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A fun group of new friends!
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Amazing views of Crater Lake

Bottom Line Yes, I would recommend to a friend

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This was our first Backroads trip but not our last!

Submitted August 2023

By dina

From Iowa

Our leaders were amazing in every aspect of this trip and are the reason we want to do another Backroads vacation! The Bend area is beautiful and has a variety of things to offer: Good food, accommodations and things to do off your bike!

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Bottom Line Yes, I would recommend to a friend

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A great trip with my brothers

Submitted July 2023

By Craig

From PA

This was a great trip that exceeded my expectations. It was a fun experience to share with my brothers. Everything was well organized and we were well taken care of with wonderful accommodations, logistics and food. The staff was well prepared, knowledgeable, supportive, and fun to be around. The bike routes were both challenging and rewarding and we got to experience the diverse terrain of Oregon. I had a great week and would highly recommend to others.

User submitted media
On the rim of Crater Lake

Bottom Line Yes, I would recommend to a friend

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The perfect way to see the beauty of Oregon!

Submitted August 2022

By Cynthia

From Atlanta, GA

This itinerary is spectacular! Every ride was more beautiful than the last. Our leaders, Kelly, Allie, and Courtney did such an amazing job, even coming up with the perfect plan B on a rainy day: a picnic and wine tasting at a lovely local vineyard. I would highly recommend this trip to anyone wanting to see just how blue Crater Lake really is!

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Girls' trip: Cheaper than therapy!
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Beautiful ride!
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Backroads' picnics are the best!

Bottom Line Yes, I would recommend to a friend

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Great tour that both avid &more casual cyclists will enjoy

Submitted July 2022

By Greggy

From Westchester, NY

This tour offered a variety of routes with different lengths, allowing both me (the avid cyclist on the performance bike) and my wife (the casual cyclist on the ebike) to enjoy the trip. Great accommodations and food, excellent support during rides. The trip leaders and support are superb.

Bottom Line Yes, I would recommend to a friend

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This is a Fabulous Trip!

Submitted July 2022

By Deb J

From Simsbury, CT

This was my first time to Oregon and the state and Bacroads did not disappoint. The guides were amazing. They worked like a well oiled machine to pull off 6 wonderful days. The accomodations and food were top notch and the biking incredible. I do not normally use an ebike, but I did on this trip mostly because I live on the east coast and am not used to the elevation gains. It was the right decision and would not hesitate to use one on future trips, I would highly recommend this trip!

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Glorious Day at Crator Lake!

Bottom Line Yes, I would recommend to a friend

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One of the best trips I've ever taken

Submitted October 2021

By Babs

From Punta Gorda, FL

The 3 guides were execeptional, the food fantastic and the accomodations delightful. I was concerned the biking would be too much for me, although I'm fit I have done very little biking. However having the e-assist bike made biking in the mountains joyful rather than the ordeal I anticipated. The other guests were friendly and always asked if we were okay if we stopped on side of the road. The scenery was spectacular and more varied than I anticipated. GREAT Trip!

Bottom Line Yes, I would recommend to a friend

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This trip was awesome

Submitted August 2021

By carmen

From nashville

The central Oregon area: sisters, deschutes, crater lake, mackenzie pass- is beautiful. I want to go back already.

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Smith rock
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Andrew Backroads leader fixed my tire in < 3min
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Crater lake about 10 miles in
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Crater lake lodge view
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Mckenzie pass
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Alpacas in central oregon

Bottom Line Yes, I would recommend to a friend

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Our Oregon-Crater Lake Bike Trip was Outstanding!

Submitted August 2021

By Barry

From Chicago IL

Our trip leaders Jason, Eliav, and Jackie were exceptional. They were confident, professional, energetic, fun, experienced and safe. They were passionate and helpful. They attended to every detail, and made sure guests had a fantastic trip. In particular we loved the views, the biking, the hotels, the dinners, etc. Crater Lake is gorgeous. The biking around Bend is terrific. Thank you! Highly recommend!

Bottom Line Yes, I would recommend to a friend

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From $4,099 /person

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Dates & Prices

Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.

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Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

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From $4,099 /person

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