Oregon's Bend Multi-Adventure Tour - Weekend Getaway

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)

Activity Levels 1-3

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We rate our trips based on a range of activity levels from 1-5.

Activity Levels None (Black)

See this trip's Activity Options & Terrain for more details.

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

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Oregon's Bend Multi-Adventure Tour - Weekend Getaway

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)

Activity Levels 1-3

Tooltip Desktop

We rate our trips based on a range of activity levels from 1-5.

Activity Levels None (White)

See this trip's Activity Options & Terrain for more details.

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

Mountain Town Charms, Smith Rock & the Deschutes River

Escape to iconic Oregon landscapes on an epic getaway. Establish base camp in Bend. Raft the Deschutes and hike Smith Rock’s craggy peaks. Bike country roads to a local taproom. Adventure’s calling. Let’s go.

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Bike
Hike/Walk
Raft

Highlights

  • Enjoy world-class cycling through Central Oregon’s rugged landscapes, with sensational scenery at every turn
  • Explore walkable, woodsy downtown Bend, with its thriving arts and culture scene, specialty stores featuring handcrafted goods and welcoming outdoor spaces
  • Discover high desert hiking trails and postcard-perfect views of the Cascade Mountains at Smith Rock State Park
  • Ride the Deschutes River’s Class II-III rapids surrounded by lava fields and ponderosa forest—a rip-roaring good time!
  • Celebrate Bends legendary food and brew culture with a locally sourced lunch and a frosty pint after a day on the trail or in the saddle
Oregon Bend Multi-Adventure Tour - Weekend Getaway 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 and one woman riding bicycles on an asphalt road, next to a river

Day 1

Description

Bike a scenic loop from Bend—you’ll quickly see why it’s a ride loved by locals • Soak up expansive views of the Cascades as you spin past sprawling ranchland, dense pine forest and across the Deschutes River, designated a National Wild and Scenic River • Pop by one of Oregon’s legendary food trucks for lunch before exploring downtown Bend, Oregons adventure capital • Stroll down charming streets packed with art galleries and cafés • Settle into our eco-chic hotel in the heart of this beloved city.

Accommodations

Nights 1-2

The Oxford Hotel
Bend
*Deluxe Hotel

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

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
Group of men and women hiking on a dirt trail with large mountains in the background

Day 2

Description

Hike in Smith Rock State Park, where the Crooked River runs through the heart of a unique tableau of cliffs and rock spires • Surrounded by majestic mountain views and a striking rugged landscape, it’s easy to imagine how sport climbing was born here • Thirsty? Find out what’s on tap at over 20 local craft breweries • Or skip the beer garden and head to the river for a favorite local pastime • Cap off the day with some quality time in the sauna or steam room at our welcoming retreat.

Accommodations

Nights 1-2

The Oxford Hotel
Bend
*Deluxe Hotel

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

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
Group of people paddling on a red raft in a river

Day 3

Description

Set out for an exhilarating rafting trip down the Upper Deschutes River • Paddle renowned Class II–III rapids, including the Big Eddy, as you wind through peaceful woodlands and breathtaking lava fields • Toast your adventure at one of Bend’s most beloved breweries.

Accommodations

Nights 1-2

The Oxford Hotel
Bend
*Deluxe Hotel

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

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

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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Hotels

Deluxe Hotels

Our Deluxe hotels have great ambience and modern comforts.

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

Nights 1-2

The Oxford Hotel
Bend

*Deluxe Hotel

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

Return

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Dates & Prices

Dates Coming Soon

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

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