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Trip Itinerary
Experience one of America's most dynamic landscapes by bike, from Crater Lake's volcanic peaks to the high desert of Bend and Sisters.
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Where to Arrive
Airport:
Redmond Municipal Airport - Roberts Field (RDM)
Pick-up location:
The Oxford Hotel, Bend, Oregon
Pick-up time:
8:00 AM
Where to Depart
Airport:
Redmond Municipal Airport - Roberts Field (RDM)
Drop-off location:
Redmond Municipal Airport - Roberts Field (RDM)
Drop-off time:
11:30 AM
Additional Arrival Information
We suggest that you arrive at least one day prior to the start of your Oregon cycling tour, 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. Once you have arrived in Redmond, there are several options for getting to your pre-trip accommodations. If you wish to schedule a shuttle prior to arrival we recommend reaching out to Enviro Shuttle (www.enviroshuttle.net or 541-598-5384). Alternatively, you may call a taxi from the airport upon arrival for your transportation. Bend, where your trip begins, is located about 30 minutes south of the Redmond Airport. If you need a place to leave your personal vehicle for the week, you may valet your vehicle with the bellman at the Oxford for $32/day. Or alternatively, there is a public parking deck behind The Oxford Hotel which has a rate of $10 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 have your first day's cycling clothes and gear easily accessible, separate from your luggage (you will have the opportunity to change into your cycling clothes upon arrival to the lunch location). A two and a half hour shuttle will take you to your first destination deep in the Cascades—Crater Lake National Park. After lunch with the group, you will receive a personal bike fit to ensure a smooth and comfortable ride. Afterward, your guides will present information on safety and equipment usage along with an overview of the day’s ride. Then you’ll set out for a ride along 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. If you cannot reach them, please call our first hotel, Crater Lake Lodge (866-292-6720), 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 shuttle 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.
Additional Departure Information
You will say farewell to your guides at 11:00 AM at FivePine Lodge. You will then shuttle 30 minutes to Redmond, arriving around 11:30 AM to 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 The Oxford Hotel in downtown Bend.
Visit Crater Lake National Park
Overview
Welcome to the first day of your Crater Lake bike tour! After a scenic two and half hour shuttle into Crater Lake National Park, you'll be welcomed with a delicious lunch provided by your guides. After a brief orientation, safety talk, and getting comfortably fit to your Trek bike, 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 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 42 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 incredible view after the next. After this stunning ride, you'll get to know one another better during a social hour, followed by dinner in the Crater Lake Lodge dining room before retiring to your room for a well-earned rest.
Please note: Due to ongoing construction on East Rim Drive, riding the entire loop around the Crater Lake Rim will not be possible for several years, hence the out and back route to Cloudcap. Also, while the location is unparalleled, the accommodations at Crater Lake Lodge are rustic and feature basic amenities.
Hotel
Crater Lake Lodge
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
Social hour overlooking the lake
Gather on the patio at the Crater Lake Lodge for a fun social hour. Take in stunning views of the evening light over the lake while enjoying hors d’oeuvres and drinks, as your guides fill you in on the exciting details of the days to come.
Ride Options
Ride Option 1
TODAY'S RIDE:
Crater Lake Lodge to Cloudcap Return - Approximately 37 mi | 60 km and 4,270 ft | 1,302 m
Ride Option 2
SHORT OPTION:
Crater Lake Lodge to Cloudcap - Approximately 19 mi | 31 km and 2,480 ft | 756 m
Ride the Cascade Lakes Highway to the cycling mecca that is Bend
Overview
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 Cascade 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 local's favorite Pole Pedal Paddle race route. Tonight, you'll toast with local brews or wine (included in the price of your trip) to a big day during dinner at Zydeco Kitchen & Cocktails, which serves southern-inspired dishes with an emphasis on locally-sourced ingredients.
Hotel
The Oxford Hotel
Meals included
Breakfast | Lunch | Dinner with Drinks
Highlight of the Day
Ride through the picturesque Cascades
Breathe in the pine scent as you cycle through the Cascades, past clear alpine lakes, and ascend Mt. Bachelor, a popular ski and downhill mountain biking destination.
Ride Options
Ride Option 1
TODAY'S RIDE:
Cascade Lakes Highway to Bend with hill shuttle - Approximately 53 mi | 85 km and 1,800 ft | 549 m
Ride Option 2
SHORT OPTION:
Cascade Lakes Highway to Elk Lake - Approximately 32 mi | 52 km and 1,570 ft | 479 m
Ride Option 3
AVID OPTION:
Cascade Lakes Highway to Bend - Approximately 64 mi | 103 km and 3,300 ft | 1,006 m
Cycle from Bend to Sisters, past the dramatic canyon that is Smith Rock State Park
Overview
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. Take a moment to enjoy the views and snap some photos of the Crooked River as it winds its way beneath the beautiful sheer cliffs. Then it's a short ride to the town of Terrebonne where you'll enjoy lunch at local restaurant The Pump House before continuing your ride 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 Spa at FivePine 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 Oregon bike tour. This evening, you are free to explore the restaurants in downtown Sisters for a dinner of your choice.
Hotel
FivePine Lodge and Shibui Spa
Meals included
Breakfast | Lunch
Highlight of the Day
View the famous Smith Rock State Park
After riding through the high desert, you'll approach massive rock walls that seem very out of place in this terrain. Smith Rock's unique geological history makes this park very special to locals and rock climbers alike.
Ride Options
Ride Option 1
TODAY'S RIDE:
Bend to Rainshadow Organics - Approximately 51 mi | 82 km and 1,560 ft | 476 m
Ride Option 2
SHORT OPTION:
Bend to Terrebonne - Approximately 39 mi | 63 km and 1,160 ft | 354 m
Ride Option 3
AVID OPTION:
Bend to Sisters - Approximately 65 mi | 104 km and 2,070 ft | 690 m
Experience the famous McKenzie Highway
Overview
McKenzie Pass is a gateway between the dry and the wet sides of the Cascades, and it 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 features 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 for lunch at a shaded campground along Lost Creek. Afterwards you may choose to 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 will shuttle to Rainshadow Organics, where you will enjoy an authentic farm-to-table experience. Your visit begins with a private tour of the farm, during which you will learn about the regenerative and organic agricultural practices that makes food from Rainshadow so unique and delicious. Afterward, enjoy a social hour and multi-course meal of seasonal farm-fresh ingredients on the porch.
Hotel
FivePine Lodge and Shibui Spa
Meals included
Breakfast | Lunch | Social Hour | Dinner
Highlight of the Day
Featured Meal | Evening at Rainshadow Organics
Located on 200 acres near Terrebonne, this beautiful full-diet farm offers a variety of certified organic vegetables, herbs, berries, meats, eggs, and grains. Its engaging staff provide not only amazing food, but also hospitality and an appreciation for what makes this regenerative farm so special. Enjoy a fresh, chef-prepared meal while learning about their inspiring farming practices.
Ride Options
Ride Option 1
TODAY'S RIDE:
Sisters to Limberlost Campground - Approximately 37 mi | 60 km and 2,380 ft | 725 m
Ride Option 2
AVID OPTION:
Sisters to Limberlost Campground Return - Approximately 73 mi | 117 km and 6,080 ft | 1,853 m
Activities
Activity 1
TODAY'S ACTIVITY:
Farm Tour at Rainshadow Organics
Say farewell to Oregon with a morning ride along Indian Ford Road
Overview
This morning offers an opportunity for a final ride to round out your Central Oregon cycling trip. Venturing through the ranchlands of the high desert, today’s miles offer the chance to take one more deep breath of rejuvenating sage-soaked air and snap any final photos of the Cascades 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.
Meals included
Breakfast
Highlight of the Day
Ride Options
Ride Option 1
TODAY'S RIDE:
Indian Ford Return - Approximately 21 mi | 33 km and 520 ft | 173 m
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
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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).
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).
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).
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).
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.
Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.
Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.
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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