Oregon's Cascades & Crater Lake Family Multi-Adventure Tour

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 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 Family Multi-Adventure Tour

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 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-Aug

National Park Playground in the Pacific Northwest

Forested hiking trails and scenic byways, bikeways and waterways. America’s deepest blue lake. The brews and the views. We can barely contain our excitement about Oregon! Can you?

... Read more
Biking
Walk/Hike
Raft

Highlights

  • Hike the high-desert trails of Smith Rock for out-of-this-world views of the Cascade Mountains
  • Explore Bend, Oregon's adventure playground, with more breweries per capita than anywhere else in the state 

  • Bike the rim of Crater Lake's world-famous caldera—one of the most spectacular rides in America

  • A rafting trip down a section of the Deschutes River promises thrills and plenty of fun

  • Experience a burgeoning farm-to-table and craft beer scene, with daily opportunities to taste the best of the region 
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

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 scenic Smith Rock State Park, follow a trail alongside the Crooked River and 800-foot cliffs 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.

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

Nights 3-4

Sunriver Resort
Sunriver
Premiere Hotel

Situated in the pristine natural setting of the Cascade Range foothills, this top-notch 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.

Days 5-6

Description

Welcome to Crater Lake National Park—ready to ride the iconic Rim Drive? • As you pedal along the rim 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 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.

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 $4,499 /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 top-notch 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 classic national park lodge transports you to a bygone era.

From $4,499 /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+

From $4,499 /person

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From $4,499 /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.

Unplugged dates are perfect for guests who want to ride an acoustic bike.
E-bikes are available to travel companions by request only.

Your guest & room selections

1 adult

1 room, 1 bed

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Please Select a Group Size

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

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!

Download & Share

Book with Confidence

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

Learn more

From $4,499 /person

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