Pedal past snow-capped volcanic peaks that scrape the sky as you cycle from crystal blue Crater Lake to the recreation mecca of Bend and Sisters, Oregon. Exploring the Oregon Cascades on bike, foot, and boat is how it’s done - allowing you to fully experience the drama and nuances of this dynamic landscape on a fully supported vacation of a lifetime. While outdoor activities - such as rock-climbing, golfing, and rafting - are a true highlight of Central Oregon active travel, your luxury biking vacation will showcase that indoor activities - spa treatments, gourmet dining, pampering accommodations, and ubiquitous microbreweries - are just as thrilling on this exceptional bicycling tour.
View Itinerary»
Trip Wow’s
- Ride around the deepest, clearest Alpine Lake in the US at Crater Lake.
- Enjoy organic northwest cuisine, complemented by local Pinots, microbrews, cheeses, and produce.
- Try many outdoor activities - from hiking and mountain biking to rafting and golfing.
- Experience the geologic wonders of volcanic lakes, caves, canyons, and high peaks.
- Imbibe in the "living the dream" culture that makes Central Oregon a great place to live, play, and visit.
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Days 1 & 2 | Crater Lake
Stay at Crater Lake Lodge
Ride up the slopes of ancient Mt. Mazama - its volcanic eruption created Crater Lake | Cruise the Rim Road, viewing the world’s deepest alpine lake from 360 degrees | Hike into the dormant crater to catch a boat cruise on the surface of the crystal blue water with record-setting140-foot visibility | Explore the lush temperate forests with towering trees, wild flowers, and trickling 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 Cascades Cycling Classic
Day’s 5 & 6 | Bend, Smith Rock, Sisters and the McKenzie Pass
Stay at Five Pine Lodge and Shibui Spa
Cycle through farms and ranches, beneath volcanoes like the Three sisters, Mt. Washington, Mt. Jefferson, and on a clear day - Mt. Hood | Hike or hire a climbing guide to explore the surreal 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 a world-class river
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 beer on the porch or resting up in the comfortable and rustic rooms, than the historic Crater Lake Lodge.
The Oxford Hotel | Bend, OR
Bend’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 place not to leave at the end, or even the beginning of your day.
Five Pine Lodge and Shibui Spa | Sisters, OR
Imagine elegant and spacious contemporary craftsman-style cabins and lodge rooms and a full-service Japanese Spa, all nestled into a pine-forested meadow at the base of three extinct volcanic peaks, and you have just begun to describe the Five Pine Lodge. This is more than a hotel - it is a mountain retreat from which you will not want to leave - complete with swimming pool, first-run movie theater, brew pub and world-class restaurant, full-service spa, and endless trail network for hiking or biking right out the back door. This is northwest lodging at it’s finest.
What’s Included in the Trip Price
- 5 nights of accommodation
- Daily breakfast, 5 lunches, 3 social hours, 4 dinners, and all snacks and drinks for each day
- The knowledge, support, and camaraderie of experienced guides
- Daily route support
- The use of a Trek Madone— 5.2 carbon road bike, or Trek Madone— 5.2 Women’s Specific Design carbon road bike (limited selection), or Trek 7.7 FX— hybrid bike
- The use of Trek bike helmets and other gear and equipment to make your ride comfortable
- Trek Travel water bottles
- Private tours
- Entrance fees to all group events/activities
- All luggage transfers
- All transportation during the trip, including private coaches
- Comprehensive trip literature and complimentary Trek merchandise
- All gratuities for special events, local guides, transfers, hotels, and restaurants
- $300 Discount on a 5 or 6 series Trek Madone purchase at your local Trek retailer
Not Included
- Airfare to and from the trip
- Transportation to the trip pick-up location
- Lodging before and after the trip
- Gratuities for Trek Travel guides
- Personal items purchased during the trip
- Some meals are not included in each destination, which allows you the opportunity to explore regional cuisine on your own. Your guides are happy to make recommendations should you so desire.
What is the weather going to be like?
Summer in Central Oregon is THE time to be here, with crystal clear blue sky days and very low humidity (10-20%). Day temperatures can be pleasant to hot (high 70’s to mid 90’s) with evenings dropping to the high 30’s at Crater Lake to the low 50’s in Bend. Rain is infrequent, but it’s always good to be prepared for the occasional thunderstorm.
What are the daily rides like?
| Rider Type | 3 |
Average Daily Mileage | 41 |
| Terrain | hilly |
Average Daily Elevation | 2,300 |
On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Crater Lake & the Oregon Cascades is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer. The terrain is varied with rolling hills, some sustained climbing (up to 18 mi.) at elevation (up to 7700 ft) on moderate grades (up to 9 percent). See Itinerary for specific daily ride distance and elevation options.
What are the options for a non-rider travel companion?
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip—please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. See Included In The Trip Price for more information.
Some non-riding options on this trip are:
- Hike and take a boat on Crater Lake
- Swim and canoe on Elk Lake
- Hike Green Lakes Trail
- Raft or Canoe the Deschutes River
- Golf in and around Bend and Sisters
- Shop in Bend and Sisters
- Spas in Bend and Sisters
- Rock Climb Smith Rock
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.
| Trip | Dates | Price (USD) |
| Crater Lakes & Oregon Cascades |
Jul 15-20, 2012 | Guaranteed Date
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$2,895 per person | $750 single occ. |
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Jul 22-27, 2012 |
$2,895 per person | $750 single occ. |
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Jul 29-Aug 3, 2012 |
$2,895 per person | $750 single occ. |
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Aug 5-10, 2012 |
$2,895 per person | $750 single occ. |
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Aug 12-17, 2012 |
$2,895 per person | $750 single occ. |

Want to travel with your with friends, family, or colleagues? We can make any trip private. More»

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Wow’s From Our Guests & More Photos
When we asked our guests what their favorite WOW's were from their Crater Lake & the Oregon Cascades bike vacations, here is what they said…
Beautiful rides, great climbs, final day ride with stop in Belknap Hot Springs was a perfect ending.—Pat
They are always well organized with great guides making it a hassle free vacation. See ya again next year.—Debbie