Crater Lake & Oregon Cascades

West Coast


Crater Lake & Oregon Cascades

Experience the Oregon Cascades and Crater Lake on a fully supported bike tour of a lifetime…

Exploring the Oregon Cascades on bike, foot, and boat is the only way to fully experience the drama, nuance and wonder of this dynamic landscape on a fully supported cycling vacation of a lifetime. Pedal past snow-capped volcanic peaks that scrape the sky as you cycle from crystal blue Crater Lake to the recreation meccas of Bend and Sisters, Oregon. While outdoor activities are a true highlight of Central Oregon active travel, your luxury vacation will demonstrate that indoor activities such as spa treatments, gourmet dining, pampering accommodations and unique microbreweries are just as important on this exceptional bicycling adventure!…

2014 Dates

Aug /

2015 Dates

Jul / Aug /
See all dates



Group Discounts [?]

Rider Type [?]



Hotel Style [?]



Start | End

Redmond, Oregon


6 days | 5 nights

Beyond Biking

Hiking, Historical Site Visit, Boat Cruise, Shopping

DAYs 1 & 2

Crater Lake

Stay at Crater Lake Lodge

Ride up the slopes of ancient Mt. Mazama—whose volcanic eruption created Crater Lake | Cruise the Rim Road to witness one of the world's deepest alpine lakes from 360 degrees | Hike into the dormant crater to catch a boat cruise on the surface of the crystal blue water | Explore lush temperate forests with towering trees, wild flowers, and glittering streams

DAYs 3 & 4

Cascade Lakes Highway to Bend

Stay at The Oxford Hotel

Cycle through tall pine forests, between dramatic peaks and crystal blue lakes, along the serene Cascade Lakes Highway | Swim or boat on picturesque Elk Lake | Explore the many adventures in and surrounding Bend - including hiking, rafting, rock climbing, mountain biking, and more | Check out the boutiques and galleries in Bend, take a brewery tour, or get a hot-stone massage | Ride a classic high-desert loop—often part of the Cascade Cycling Classic

DAYs 5 & 6

Smith Rock, Sisters and McKenzie Pass

Stay at Five Pine Lodge and Shibui Spa

Cycle through farms and ranches, beneath volcanoes like the Three Sisters, Mt. Washington, and Mt. Jefferson | Hike or hire a climbing guide to explore the surreal rock formations at Smith Rock State Park | Enjoy the peaceful forest, luxurious rooms, or the award-winning spa at Five Pine Lodge in Sisters | Climb the spectacular McKenzie Highway over expansive lava fields and down into lush forests, along the gorgeous McKenzie River


Dates & Pricing


10th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC.
17th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC.


5th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
12th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
19th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
26th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
2nd / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
9th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14
16th / 6 days / 5 nights
$2999 / Person, $750 / Single OCC. / 2014 pricing until 8/1/14, Alternate Hotel

Crater Lake Lodge on Trek Travel's Oregon bike tours

Crater Lake Lodge

Crater Lake National Park, OR

Perched on the rim of Crater Lake, you will find no better place to take in the majestic view while relaxing with a drink on the porch or resting up in the comfortable and rustic rooms than the historic and truly Northwestern Crater Lake Lodge.
Oxford Hotel on Trek Travel's Oregon bike tours

The Oxford Hotel

Bend, OR

Trip Advisor and Trek TravelBend's "eco-chic" boutique hotel is the pinnacle of luxury and sustainability. Fusing Northwest-inspired, modern design, world-class service and earth-friendly practices and products, the Oxford is a perfect match for the active and cosmopolitan vibe that is Bend, Oregon. Located in the heart of downtown, shopping, dining, galleries and a variety of activities are just a few steps or a cruiser ride away (provided with your stay). Amenities like the sauna, spa, full-service bar and restaurant, as well as room service, make it the perfect home for your time in Bend.
Five Pine Lodge and Shibui Spa on Trek Travel's Oregon bike tours

Five Pine Lodge and Shibui Spa

Sisters, OR

Trip Advisor and Trek TravelImagine elegant and spacious contemporary Craftsman-style cabins and lodge rooms combined with a full-service Japanese Spa, all nestled into a pine forest at the base of three extinct volcanic peaks. You have just begun to picture the Five Pine Lodge. This is more than a lodge—it is a true mountain retreat from which you will not want to leave—complete with swimming pool, first-run movie theater, brew pub and an extensive trail network for hiking or biking right out the back door.

What's Included in the Trip Price?

What's not Included?

What is the weather going to be like?

What are the daily rides like?

What are the options for a non-rider travel companion?

General FAQs

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Our Guides

Besides our many options in travel styles, dates, prices and destinations, we also accommodate your vacation style each day of your trip. You decide how to spend your time whether it is with the group or exploring on your own, riding a little, a lot, or not at all.

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the full-carbon, ultra smooth Trek Domane 5.9, to the comfortable Trek 7.6 FX Hybrid–both included in the trip cost, to our numerous upgrade options, you deserve the best ride on your vacation.

Your Day. You decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.


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