Oregon's Cascades & Crater Lake Multi-Adventure Tour

Couples, Friends & Solos
Couples, Friends & Solos
ALSO AVAILABLE FOR:
Families with 20s & Beyond

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

30s & 40s Adults 30-49

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 1-4

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 Multi-Adventure Tour

Couples, Friends & Solos
Couples, Friends & Solos
ALSO AVAILABLE FOR:
Families with 20s & Beyond

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

30s & 40s Adults 30-49

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 1-4

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: Jul-Sep2026: Jun-Sep

National Park Playground in the Pacific Northwest

Hike forested river trails, bike scenic byways and raft the rollicking Deschutes. Ponder Crater Lake’s deep blue waters. If you’re looking for both excitement and awe, you’ll find it in Oregon’s Cascades.

... Read more
Bike
Walk/Hike
Raft

Highlights

  • Bike along the Cascade Lakes Scenic Byway into the Deschutes National Forest—a favorite route of local cyclists
  • Rafting the Deschutes River—this ride will get your adrenaline pumping!
  • Hike the high desert trails of Smith Rock State Park—the birthplace of sport climbing—for out-of-this-world views of the Cascade Mountains 
  • Bend!—Oregon’s adventure playground is known for its innovative food scene and for having more breweries per capita than anywhere else in the state
  • Take a spin on Crater Lake’s world-famous Rim Drive—one of the most spectacular rides in America 
  • Read More
Oregon Cascades & Crater Lake Multi-Adventure 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

Two men with walking poles, hiking on a dirt trail next to a canyon

Days 1-2

Description

Cycle through Central Oregon, tracing the mighty Deschutes River • Cruise into Bend, the state’s adventure capital, then park your bike and see what’s on tap at a local craft brewery • Hike in Oregon’s rugged high desert wonderland of sagebrush and rock spires • At Smith Rock State Park, follow a trail alongside the Crooked River or ascend Misery Ridge for closer views of colorful Red Wall and Monkey Face, popular among rock climbers • Spend a leisurely afternoon in downtown Bend perusing shops and galleries, or take a dip in the Deschutes River. 

Accommodations

Nights 1-2

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.
Group of people on a red rafting, paddling through a river

Days 3-4

Description

Bike into the heart of the Cascades on a favorite ride of locals • Enjoy lunch and panoramic views of the Three Sisters—closely spaced volcanic peaks—from the top of Mount Bachelor • Meander along a riverside trail, watching placid waters transform into dramatic waterfalls • Raft through Class II–III rapids as the Deschutes winds through lush woodland.

Accommodations
Sunriver Resort

(2 nights)

Nights 3-4

Sunriver Resort
Sunriver
Premiere Hotel

Situated in the pristine natural setting of the Cascade Range foothills, this resort is a mecca for outdoor enthusiasts and culinary aficionados. (pool, spa)

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Group of people biking on a road, looking to the left towards a large lake

Days 5-6

Description

Welcome to Crater Lake National Park—ready to experience the iconic Rim Drive? • You can’t help but be awestruck by the lake’s intense sapphire color and amazing clarity as you pedal along the rim of this enormous caldera • 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 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

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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.

From $4,599 /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

The Oxford Hotel
Bend

Premiere Hotel

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

Nights 3-4

Sunriver Resort
Sunriver

Premiere Hotel

Situated in the pristine natural setting of the Cascade Range foothills, this resort is a mecca for outdoor enthusiasts and culinary aficionados. (pool, spa)

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 $4,599 /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 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+

From $4,599 /person

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Reviewed by 15 customers

Great family trip!

Submitted November 2024

By Susan

From Massachusetts

We took the whole family as a graduation celebration and had a blast! Multi-adventure was a perfect mix of biking and hiking and the tubing and rafting.were SO MUCh FUN! And Crater Lake was spectacular! The leaders were wonderful - such a great support to everyone on the trip, regardless of where they were at on level of activity. Thank you, Backroads!,

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Work Hard...Play Hard!

Submitted August 2023

By sandi

From Tallahassee, FL

Had so much fun on this trip. It challenged me but I loved it! I liked having the options to do longer or shorter rides and hikes. We didn't start too early, and we didn't end too late. We had the late afternoon to relax before dinner. The places we stayed were awesome and the food was great! The leaders were so attentive and helpful. They were lots of fun and I could tell they really enjoyed what they do!

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Faith and Eliav

Bottom Line Yes, I would recommend to a friend

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Challenging and exhilarating

Submitted July 2023

By Susan K

From Raleigh, NC

Great variety of activities with a challenging bike ride up Mt Bachelor rewarded by incredible views at the summit., white water rafting down the Deschutes, and gorgeous hikes around Crater Lake and Smith Rock. The trip leaders were always just around the bend with support and snacks and gourmet trail lunches that appeared out of thin air. Hotels right in the heart of Bend and in a more rustic resort setting provided a nice mix of styles for all

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Deschutes National Forest

Bottom Line Yes, I would recommend to a friend

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We love the multi-sport trips -- this one was excellent!

Submitted August 2022

By Vicky

From Pittsburgh

Backroads leaders are exceptional people and are unbelievably impressive. They make all the difference in the quality of the experience. I loved having a pedal-assisted e-bike so I could be challenged and get exercise, but it enabled me to ride with my husband who wasn't on an e-bike. The hiking and biking were wonderful. The scenery was breathtaking. We can't wait to go on our next Backroads trip.

Bottom Line Yes, I would recommend to a friend

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Another outstanding trip

Submitted August 2022

By deborah

From Albany, ny

Beautiful vistas, great leaders , fun kids (and adult) activities and ad always great leaders.

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Crater lake

Bottom Line Yes, I would recommend to a friend

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My 9th Backroads trip and one of my favorites

Submitted July 2022

By Mackensie

From Atlanta, GA

Such a fun trip! We took the 20s and beyond trip and the group and leaders were beyond incredible. Riding around the rim of Crater Lake was a thing I didn't even realize was on my bucket list, and the hikes were super great too. Amazing accommodations as well. Thank you for another amazing time, Backroads!

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Hike at Crater Lake!

Bottom Line Yes, I would recommend to a friend

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Our trip far exceeded our expectations

Submitted July 2022

By Amy

From Orlando

Our leaders were the best! Oregon is a state that should be experienced via biking. Stunning scenery that takes your breath away!

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We all conquered Misery Ridge at Smith Rock State Park

Bottom Line Yes, I would recommend to a friend

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I can't think of a better way to explore Central Oregon

Submitted June 2022

By Scott

From Indiana

From top to bottom, Backroads nailed it! Central Oregon is absolutely beautiful. So much fun to ride and hike through the varied terrain. I'm not a biker, so the thought of some of the rides seemed a bit daunting. But Backroads gives lots of options and our leaders made me feel comfortable enough to push myself and achieve more than I thought I could. The accommodations were first class. Great food, great locations and great beds (other than Crater Lake)! But even with lousy beds, what a joy to be able to stay right there at Crater Lake. Watching the sun rise over the lake is truly breathtaking. Last, but really should be first, are the Backroads leaders. In so many ways they made the trip. As you would expect, they know the area and the various activities like the back of their hands. But what really stands out is their commitment to ensuring each member in the group has a phenomenal experience. From spur of the moment sledding on card board boxes and picnic table covers, to ribbing a guy for drinking Bud Light in the craft beer capital of America and then making sure there were always a couple cans of Bud Light in the beer cooler at the end of each activity. They really do think of everything. Jason, Shauna, Eliza and Morgan, you're the best. Thank You!

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Crater Lake Sunrise June 2022

Bottom Line Yes, I would recommend to a friend

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Fabulous BR trip. Highly recommend!!

Submitted October 2021

By Lindsey Miller

From Louisville, KY

There were 8 of us on this trip. (private group) We thought the cycling and the hiking was fabulous!! The routes were beautiful with very few cars. We all got electric bikes even though several of us are extremely experienced cyclists. Our 2 guides Eliav and Andrew were incredible!! They were over the top amazing!! This was our 5th BR trip. They have all been fabulous. Bend, Oregon is a little hard to get to in that we couldn't get any non-stop flights... had a long layover in Denver, but the trip was so worth it!!

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Crater Lake, Oregon- BR trip

Bottom Line Yes, I would recommend to a friend

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Beautiful Oregon

Submitted September 2021

By Orli

From Hollywood, FL

This was my first backroads trip and I can't wait until the next one. Our guides were outstanding, knowledgeable and motivating. The accommodations were very comfortable and the movement from one location to the next was seamless. The biking and hiking routes were beautiful and although challenging, there was always an option for modifications. There is a good amount of flexibility with downtime but for the most part it's adventure filled and non-stop fun.

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Bottom Line Yes, I would recommend to a friend

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From $4,599 /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 $4,599 /person

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