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Guest Choice: Bend, Oregon

A bustling mountain town of more than 82,000 people, Bend has made its way into the limelight and stolen the hearts of outdoor enthusiasts everywhere. With a population that has quadrupled in just two decades and a vivacious tourism economy, it’s a good thing this outdoor mecca is chalk full with enough activity for all its admirers.

On our Crater Lake and Oregon Cascades and Bend Mountain Bike vacations, not only will you have the opportunity to take in panoramic vistas of the crystal blue Crater Lake or experience world class riding on an expansive network of trails, but you will also have the chance to explore our favorite recreation destination: Bend, Oregon. Be sure to take advantage of the many adventures available in town–rafting, hiking, golf, and more–before satisfying your taste buds at one of the eclectic and delicious local eateries.
Experience the outdoor mecca of Bend, OR on a Trek Travel cycling vacation
Where To Go For Drinks: Bend is synonymous with amazing beer. With a startling abundance of world-class breweries clustered close together like the gold at the end of a big, beer rainbow, Bend has been dubbed Beer Town USA. Trek Travel guides sometimes fancy themselves as beer connoisseurs, and the unparalleled local favorite amongst our team is the renowned Deschutes Brewery. Just a 3-minute walk from your hotel, the original Deschutes Public House has been a vibrant fixture of the downtown scene since 1988. Not only can you find their very first beer–the Black Butte Porter–still brewed with craft and passion, but there are a total of 19 full-flavored taps available to satisfy your taste buds. If you’re not afraid to explore the many nuances and endless possibilities of the almighty hop, try our favorite Fresh Squeezed IPA.

Where To Go For Dinner: After sharing a round with family or friends, stroll down the block to Zydeco Kitchen & Cocktails for incredible Northwest cuisine with a southern twist. Chef Steve Halt’s from-scratch kitchen is focused on freshness and quality ingredients, and features a full gluten free menu. Arguably the most well-loved restaurant in town, and a 2014 restaurant of the year winner, Zydeco’s confident combinations such as Barbecue Shrimp & Grits or Shrimp, Andouille & Crawfish Jambalaya consistently impress even the most discerning palates. Besides, our guides are pretty sure they have the best dirty martini in town.
Visit the award-winning Zydeco Kitchen  on Trek Travel's Crater Lake cycling vacation
Where To Go Out: After a delightful meal with even better company, cap off your night out in Bend with a stroll through Drake Park on your way back to the Oxford Hotel. With one-half mile of riverfront property, this is truly the centerpiece of downtown Bend’s extensive park system. The perfect way to unwind after another adventurous day, take in the picturesque reflection of Mount Bachelor off Mirror Pond or meander along the Deschutes River while admiring the majestic ponderosa pine and deciduous hardwoods.

Check out Mirror Pond and Drake Park in Bend, Oregon on a Trek Travel cycling vacation

About Guest Choice:
You will often hear us say, “It’s your day, you decide,” because our smaller group size allows the flexibility for you to decide how your day unfolds. In addition to multiple daily ride options and shuttle flexibility, this also means that we offer ‘guest choice’ nights designed for you to indulge at a local restaurant of your choosing, or explore the local sites. Whether you want to order take-out while relaxing by the hotel pool or get dressed up for a fancy dinner in town, guest choice nights let you craft your own perfect evening.

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If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date?
Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of hotel levels, from Explorer to Luxury to Ultimate Luxury. Rest assured, no matter which level of hotel you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Level 2:

Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself