Current Offers - Crater Lake and Oregon Cascades

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Pedal through the Oregon Cascades with National Parks Unbound and immerse yourself in the stunning natural wonders of central Oregon. With soaring, snow-capped volcanic peaks, the limpid waters of Crater Lake and the cultural hotspots of Sisters and Bend, Oregon, this bicycling adventure vacation lets you fully experience this dynamic, dramatic landscape. Bike, hike, and climb through some of Oregon’s top sites and tempt your senses with plenty of gourmet dining, indulgent accommodations and delicious microbreweries. 



  • Look out from the rim of Crater Lake
  • Hike through Smith Rock State Park and witness volcanic peaks, fathomless caverns and alpine lakes
  • Cycle alongside Cascade Lakes Highway alongside stunning geologic wonders
  • Wander the streets of Bend, Oregon and experience their engaging outdoorsy culture

Images & Videos

Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades
Crater Lake Oregon Cascades


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Day 1

Welcome to central Oregon! Begin your epic outdoor adventure with a scenic drive into Crater Lake National Park and a gourmet picnic lunch. After a short safety orientation, hop onto your bike for a ride along Crater Lake’s rim. It’s a stunning ride around one of the deepest lakes in the world with plenty of hiking trails and viewpoints inviting you off the road.

After your ride, enjoy cocktails and a delicious dinner at Crater Lake Lodge before heading to bed. 

Ride: Approximately 33 miles with 4,050 feet of climbing; or 22 miles with 3,000 feet of climbing

ACCOMMODATION : Crater Lake Lodge
MEALS INCLUDED : Lunch, Dinner

Day 2

After a hearty breakfast, enjoy a drive north before setting off on the day’s pedal along the Cascade Lakes Highway. The ride comes with views of the mountain range’s eastern slopes and weaves among 14 limpid lakes—on whose surface you can often see reflections of Broken Top, Mt. Bachelor and Three Sisters.

Take a break with a refreshing lunch at Elk Lake Resort featuring plenty of local produce. You can also cool off with an energizing dip in one of the Cascade Lakes and truly find yourself immersed in nature. Once we’ve finished lunch, we continue our ride with an uphill climb up Mt. Bachelor and then a rushing descent into Bend along the Pole Pedal Paddle race route.

Enjoy some local brews in Bend after your full day and a delicious southern-inspired dinner at Zydeko Kitchen & Cocktails.

Ride: Approximately 47 miles with 2,500 of climbing; Approximately 36 miles with 1,800 feet of climbing; or Approximately 69 miles with 3,500 feet of climbing 

ACCOMMODATION : The Oxford Hotel
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 3

Choose your own Bend adventure today! As an outdoor recreation destination location, Bend offers plenty to do and explore. Rent some mountain bikes and pedal Phil’s Trail system, take a hike along the Deschutes River Trail or raft down the Class 2-3 rapids of the Deschutes River. You can float or canoe down the town’s nearby river or play a round of golf at one of their tip-top courses. If you want to see what other delights Bend has to offer, check out the local breweries or indulge in a spa day. It’s your day to play, and our guides have plenty of suggestions. If you find yourself longing for a nice bike ride, check out the road to the Tumalo watershed, with a possible hike to Tumalo Falls.

See what nightlife and dining experiences Bend has to offer on your own before bed.

Ride: Approximately 23 miles with 1,400 feet of climbing 

ACCOMMODATION : The Oxford Hotel

Day 4

After breakfast, hop back onto your bike for a ride deep into central Oregon’s high desert. We stop for lunch at the dramatic cliffs of Smith Rock State Park. There’s plenty of adventure options for you today in this incredible area. You may hike along network of trails through Smith Rock’s canyon and see the hosts of climbers taking on breathtaking routs such as Voyage of the Cowdog or Monkey face. If you want to experience that rush yourself, schedule a climbing lesson. Also, you can opt to do some more pedaling with a ride through the country into the pine forest surrounding the Sisters. You also have the opportunity to fit in some relaxation and have a spa appointment at Shibui at Five Pine Lodge.

Enjoy your day of adventure and fun before rejoining with the group for dinner at a local hotspot in Sisters.

Ride: Approximately 35 miles with 1,200 feet of climbing
Longer Option: Approximately 65 miles with 2,275 feet of climbing 
Hike: Approximately 4 miles with 950 feet of climbing 

ACCOMMODATION : Five Pine Lodge and Shibui Spa
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 5

We take on one of the most popular bike rides in the northwest today as we head along McKenzie Pass and into the Cascades. We climb for about 16 miles with incredible views of towering Cascade peaks like Mt. Hood and lava flows. We celebrate conquering the pass with a stop at the Dee Wright Observatory—an excellent viewpoint as well—before heading out for the blissful 22-mile downhill stretch through thick forests.

Your ride takes you to the McKenzie River, one of the region’s most famous rivers. Stop for lunch at Belknap Hot Springs and relax with a nice soak. Then, you may either once again take on the pass for a challenging, yet stunning, climb or settle in for the ride back to Sisters.

Rejoin with the group this evening for the trip’s last happy hour and farewell dinner at Sister’s Latigo.

Ride: Approximately 39 miles with 2,500 feet of climbing
Longer Option: Approximately 78 miles with 6,400 feet of climbing 

ACCOMMODATION : Five Pine Lodge and Shibui Spa
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 6

Today offers a final ride through smooth terrain to recover from yesterday’s McKenzie Pass. Pedal through charming ranchlands and high desert with Mt. Jefferson and Three Sisters soaring in the background. Give your legs some downtime with an easy spin or relax with a stroll though the galleries, cafes and shops of downtown Sisters before checking out.

Ride: Approximately 26 miles with 600 feet of climbing


Dates & Rates

FAQ & More

How fit do I need to be for this trip?

This trip is intended for avid cyclists who are accustomed to riding about 3-4 hours at a time, and up to 70 miles on a long day. We recommend that you feel comfortable climbing hills, mountains, and sloping terrain, with 3,500-7,000 feet of climbing on a hard day. 

What should I pack?

All guests are provided with a packing list prior to their trip. 

How difficult is the terrain?

This trip starts at a high elevation (around 8,000 feet), so the Day 1 ride can feel like a bit of a challenge. However, there are plenty of opportunities to adjust mileage and duration of rides throughout the week. This trip is intended for moderate to strong cyclists. 

What are the daily rides like?

Average Daily Mileage | 33
Terrain | Hilly
Average Daily Elevation | 1,900 ft.
We strive to find paved secondary roads or bike paths and try to avoid busy roads when possible. We can also accommodate guests who seek less mileage or fewer uphills with a ride in the support van as needed. Ask about our electric bike as well 

What is the weather like

Summer is one of the best time to visit Oregon, typically the sky is a clear blue combined and the humidity is low. Daytime temperatures range from mid 70's to mid 90's with the evening time temperatures dropping to the high 30's at Crater Lake and the low 50's in Bend. Rain is not common, but it's always good to be prepared for the occasional thunderstorm.

What kind of bikes do you offer?

Your vacation includes the use of some of the best bikes on the market. On most of our destinations you’ll select between the Trek Domane 5.9, the Trek 7.6 FX and the Trek Electric Assist XM700+. Visit the Trek website for more specifics about these bikes. 

Custom or Private

You love this itinerary but want to change it a bit to make it perfect for you?  Or, are you wanting to simply make it private?  Either way, we can do it!

Fill out this quick form to begin a custom or private adventure of a lifetime:

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