- 10+ Guests Price as advertised*
- 8-9 Guests +$500 per person to trip price*
- 6-7 Guests +$1,000 per person to trip price*
- 4-5 Guests +$1,500 per person to trip price*
- 2-3 Guests +$2,500 per person to trip price*
Welcome to the first day of your central Oregon vacation! After a scenic 2-hour shuttle into Crater Lake National Park, you'll be welcomed with a gourmet Trek Travel picnic. After a brief orientation and safety talk, you’ll saddle up to begin the day’s ride along the rim road that overlooks the lake’s breathtaking blue water. The lake is one of the deepest in the world at almost 2,000 feet and was formed about 7,700 years ago when a volcano twice as high as the current rim erupted. Experts estimate that the blast that created the lake was around 420 times more powerful than the Mt. St. Helens eruption in 1980. A wealth of viewpoints tempt you along the route, as you take in one stunning view after the next. After this treat, you'll get to know one another better over drinks and dinner in the Crater Lake Lodge dining room before retiring to your room for a well-earned rest.
Crater Lake Rim Loop
Approximately 33 miles with 4,000 feet of climbing
Crater Lake Rim Loop to Skell Head
Approximately 15 miles with 1,720 feet of climbing
Crater Lake Lodge
Lunch | Social Hour | Dinner
With Crater Lake in the rearview mirror, you'll shuttle north for an hour and a half to begin your ride along the Cascade Lakes Highway, which traces the eastern slopes of the range and winds among 14 distinct lakes. Reflections of the Three Sisters, Broken Top and Mt. Bachelor are visible on the surfaces of the lakes—these images evoke the essence of the Cascades. Midway through the ride, take a break to enjoy lunch at Elk Lake Resort. After lunch, the road climbs over the shoulder of Mt. Bachelor and descends 3,000 feet to Bend, following the bike course of the Pole Pedal Paddle race route. Tonight you'll toast with local brews to a big day and dine at local's favorite Zydeko Kitchen & Cocktails in Bend, which serves southern-inspired dishes with an emphasis on locally-sourced ingredients.
Cascade Lakes Highway: Osprey Point to Bend
Approximately 50 miles with 2,520 feet of climbing
Cascade Lakes Highway: Osprey Point to Bend with hill shuttle
Approximately 41 miles with 1,450 feet of climbing
Cascade Lakes Highway: Crescent Cutoff to Bend
Approximately 70 miles with 3,470 feet of climbing
The Oxford Hotel
Breakfast | Lunch | Social Hour | Dinner
Bend is renowned as an outdoor recreation mecca, and today is an opportunity to take advantage of one of the many available adventures, including rafting the Deschutes River (Class 2-3) (this option is included in the price of your trip); renting mountain bikes and riding the world-class Phil's Trail system; hiking the Deschutes River Trail; floating or canoeing the river near town; playing golf at one of the many area courses; visiting one of the many breweries; getting a massage or spa treatment and more. The choices are almost endless and your guides will help ensure that you have the day you want. Those interested in a morning road ride will venture out and back on a beautiful and freshly paved road that climbs into the Tumalo Creek watershed before lunch on your own in town. Also be sure to make some time today to relax in the Oxford's hot tub, sauna or steam room, located on the 7th floor of the hotel. Tonight is yours to explore downtown on your own and check out one of the many eclectic and delicious eateries.
Tumalo Creek Return
Approximately 22 miles with 1,350 feet of climbing
Whitewater Rafting on the Deschutes River or Choose your own Bend Adventure
The Oxford Hotel
This morning you'll ride deeper into the high desert before stopping for a snack break at the dramatic Smith Rock State Park. This park is well-known as a world-class climbing area and is generally regarded as the birthplace of sport climbing. Stop for a break and photo op of the Crooked River as it winds its way beneath the beautiful sheer cliffs. From here you may continue your ride to Rainshadow Organics, where you will be treated to a hot lunch prepared with farm-fresh ingredients. Take some time to tour the farm before shuttling or pedaling the final miles along quiet country roads into the pine forest of Sisters. Your hotel for the remainder of the trip is also home to one of the region's best spas, Shibui at Five Pine Lodge (spa appointments should be scheduled in advance, and anyone wishing to visit the spa this afternoon will not have time to do the post-lunch ride). Whichever ride distance you choose, this stellar day is sure to be a highlight of your Central Oregon vacation. This evening you will dine with the group at the quaint and intimate Open Door in downtown Sisters.
Bend to Rainshadow Organics
Approximately 50 miles with 1,480 feet of climbing
Bend to Sisters
Approximately 65 miles with 1,980 feet of climbing
Bend to Smith Rock State Park
Approximately 35 miles with 1,020 feet of climbing
Five Pine Lodge and Shibui Spa
Breakfast | Lunch | Dinner
McKenzie Pass is a gateway between the dry and the wet sides of the Cascades, and is perhaps the most popular road to ride in the Northwest. This morning it just happens to be right outside your back door! The 16-mile climb is a moderate grade and tops out with stunning views of expansive lava flows and magnificent views of the Cascade peaks, including Mt. Hood. The historic Dee Wright Observatory is an impressive place to take in the scenery and celebrate your conquest of the pass, because from here the next 22 miles are almost all downhill. Cruising through increasingly dense forest, you'll arrive at one of the country's most scenic rivers, the McKenzie. After lunch as a group at the Belknap Hot Springs Resort you can take a soak in the hot-spring fed pool here then shuttle back to Sisters, or tackle the pass once again from the east side for a truly epic, challenging day of climbing. This evening you and your companions will gather for a final social hour to enjoy more local brews and wine, followed by a memorable farewell dinner of artisan, "upscale ranch" dining at Chops Bistro in Sisters.
Sisters to Belknap Hot Springs
Approximately 39 miles with 2,450 feet of climbing
Sisters to Belknap Hot Springs Return
Approximately 78 miles with 6,400 feet of climbing
Five Pine Lodge and Shibui Spa
Breakfast | Lunch | Social Hour | Dinner
This morning offers an opportunity for a final ride to round out your vacation in Central Oregon. Venturing through the ranchlands of the high desert, today’s 22 miles offer the chance to take one more deep breath of rejuvenating sage-soaked air before moving on to your next adventure. Alternatively, have a long sleep-in and take a walk through downtown Sisters to explore its unique shops, galleries and cafes before check-out.
Indian Ford Return
Approximately 22 miles with 500 feet of climbing
Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.
It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019 we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More
It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More
See itinerary for specific daily ride distances and elevation options. 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. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.
Averages and totals are calculated from our "Today’s Ride" options.
We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Redmond Municipal Airport - Roberts Field (RDM) in Redmond, Oregon. This airport is served by Alaska Air, American Airlines, Delta Airlines, and United/United Express. Once you have arrived in Redmond there are several options for getting to your pre-trip accommodations. If you choose to stay at The Oxford Hotel in Bend, where you will meet your guides on the first day of your trip, the hotel offers a shuttle service for $45 each way from the airport to the hotel. Please call the hotel to schedule this service. Alternatively, you may call a taxi from the airport upon arrival for your transportation to Bend, which is located about 30 minutes south of the Redmond Airport. If you need a place to leave your personal vehicle for the week, there is a public parking deck behind The Oxford Hotel and the daily rate is $5 per day.
Your Trek Travel guides will meet you at The Oxford Hotel (10 NW Minnesota Ave, Bend) at 8:00 AM on the first day of the trip. Please arrive dressed in casual clothes and pack a day bag with your cycling clothes and gear that you can keep easily accessible. A 2 hour private shuttle will take you to your first destination deep in the Cascades-- Crater Lake National Park. After a gourmet signature Northwest picnic prepared by your guides, you will change into your cycling clothes and get a personal bike fitting to ensure a smooth and comfortable ride. Afterward your guides will present an overview of the day’s ride around Crater Lake’s dramatic rim.
If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Crater Lake Lodge (541 594 2255), and leave a message with your expected arrival time and contact details. There are no scheduled shuttle services offering direct access to Crater Lake, and while you may be able to hire a taxi or limo service, please be warned that the cost involved may be significant. We strongly recommend that you arrive the night before to ensure you do not miss our Trek Travel shuttle.View our pre hotel recommendations
You will say farewell to your guides at 11:00 AM at Five Pine Lodge. You will then shuttle 30 minutes to Redmond, arriving around 11:30 AM at the Redmond Airport. Please allow adequate connection time for flights or other travel to accommodate possible traffic delays. If you wish to return to downtown Bend to retrieve your personal vehicle or extend your stay in the area, your guides can drop you off at The Oxford Hotel following the airport drop. It is about 30 minutes from the Redmond Airport to downtown Bend.View our post hotel recommendations
Summer is the best time to visit Central Oregon, as skies are typically crystal clear blue combined with very low humidity (10-20%). Daytime temperatures can be pleasantly temperate to quite hot (high 70's to mid 90's) with evenings dropping to the high 30's at Crater Lake and the low 50's in Bend. Rain is fairly infrequent, but it's always good to be prepared for the occasional thunderstorm just in case. Packing List
The city of Bend is well-known as a mecca for lovers of all things outdoors. The vibrant downtown and Old Mill District are also great spots for eclectic dining experiences, people-watching, shopping, and local beer-tasting. With so many things to do you may just want to stay here! You can explore one of Central Oregon's rivers, fed by crystal-clear mountain snow, in a canoe or kayak. Into Golf? Central Oregon has been rated as one of the top 50 golf destinations in the world! Don't forget about the fishing, hiking and mountain biking opportunities too. We recommend the following accommodations for your pre and post-trip hotel:
Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.
Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.
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.