Home » Mountain Bike Tours » Cascade Crest: East to West

Bend or Oakridge? You’ve probably heard of both. Why not ride both on your next trip to Oregon? A mere 2 hours apart, the difference in terrain and trails make this a really fun tour. You get to experience the outdoor recreation mecca of Bend, and the quiet timber town turned mountain biking destination of Oakridge.

Bend trails might just have inspired the concept of “flow”. They are fast, swoopy and built specifically for mountain biking. The Bend area trails range from high alpine meadows to High Desert juniper and pine trees, giving you a sampling of varied ecology and scenery. Downtown Bend is full of excellent restaurants, pubs, bars and shops – plenty of great opportunities to chill out after spending all day on the trail.

Oakridge is a former timber town surrounded by steep, tree-covered mountains. With trail sections names like “Jedi Forest”, “Chrome Toilet”, and “Windy Pass”, Oakridge trails are epic, heart pounding, incredibly scenic and satisfying. Riding through Oakridge’s deep forests and steep terrain will remind you of childhood stories of prehistoric lands and mythical creatures. At the end of the day, we’ll check in to the Oakridge Lodge, within walking distance of the local pub. Bottoms up!


  • 4-days of mountain biking.
  • Local, expert and caring guides.
  • Transportation to and from Bend, at the start and end dates of tour.
  • Transportation during the tour.
  • Four nights of hotel accommodation, double to triple occupancy. (The Oakridge hotel has double rooms and family rooms – please inquire with us if interested.)
  • All breakfasts, lunches, and 3 dinners.
  • Complimentary Deschutes Brewery beer, Crater Lake Spirits and Humm Kombucha.
  • Cog Wild t-shirt & patch.

Trip Overview

Oakridge, Bend
4 Days
5 - 9
6 - 9
Tour Style
Tour, Hotel
Tour Size
12 guest maximum
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Add more to your trip

Our goal is to maximize your experience with us. Talk to us about adding more rides, staying an extra day, or finding more to do while on vacation.

2018 Dates*:

  • June 13-17
  • October 3-7

*If these dates don’t work for you, contact us to create a custom tour for you and your group of 4 or more!

Start Location: Meet at Cog Wild Headquarters at 9:00am or meet us in Oakridge.

Price: $1375
$250 single supplement fee

*Price Does Not Include:

  • 1 dinner.
  • Mountain bike rentals. You can absolutely bring your own bike, or choose to rent a bike. See our bike rentals page for more information.
  • Airport shuttles to and from the Redmond (RDM) Airport. You will need to arrange for your transportation to/from Bend (15 miles). We recommend Enviro Shuttle or Redmond Airport Shuttle.
  • Trip Insurance. We highly recommend purchasing trip insurance for the unforeseeable. See our cancellation policy below.
  • Guide gratuity. If you like the ride, tip your guide!

Cancellation Policy. Cog Wild follows the below policy for every multi-day tour guest:

    • All multi day tours will be charged a 50% deposit per person  at the time of booking, $100 of which will be non-refundable.
    • Cancellations 30-14 days prior to the tour: The participant will be required to pay 50% of trip price.
    • Cancellations within 14 days: No refund.

Riding Distance

92 – 100 miles over the 4-day vacation. Expect about 22 miles a day.




Mid-intermediate to advanced. Riders should be physically fit and have various experience and skill with mountain biking.

Terrain & Trails

The terrain and trails vary widely between Bend and Oakridge—that’s what is awesome about this tour as you get to experience a lot. Bend trails are generally fast and flowy, with a few rocks and logs thrown into the mix. Scenery on Bend area trails ranges from high cascades alpine meadows to high desert pine trees. Oakridge trails have literally everything—narrow, fast, slow, smooth, rocky, rooty and steep uphills and downhill. Expect some exposure, technical terrain and creek crossings.

Recommended Clothing & Gear

Prepare for four full days of riding, so bring adequate clothing, including layers for a variety of weather. Hydration packs are necessary for carrying food and water. Helmets are required for all rides. Bring a swimsuit for dipping in the river! Bend and Oakridge are both casual mountain towns. Bend has more upscale dining opportunities if interested.

Day 0
Arrive in Bend and check into the DoubleTree. Your guides will meet you at the DoubleTree before heading to a classic Bend restaurant for dinner. You will have time to meet everyone and get lots of rest before your ride first thing in the morning. Breakfast provided by your hotel.

Day 1
Day 1 takes you on Bend’s newest and most progressive trails in the Wanoga Trail Network. We’ll shuttle you to the top, and guide you on a variety of mountain bike specific trails back to town. You’ll be awed by views of snow capped volcanic mountains as you grind up short climbs and swoop down fast, loamy descents. We’ll be sure to stop for lunch at the best on-trail spots. Dinner is on your own at one of Bend’s many awesome dining options.
Mileage: 25 miles

Day 2
You will check out of your hotel in Bend before the ride. Load your bags into the Cog Wild van to move on to the next location. Today you’ll ride from the Cascade crest back to Bend. We’ll start at the base of Mt. Bachelor at Dutchman Flat and ride up to 35 miles of sweet singletrack bliss as we make our way back to town. This is a classic Central Oregon ride, but there are many options depending on the conditions for that day. However we go, you will sure to experience miles of fast flowing sections, rocky outcroppings, scenic alpine views, and swoopy forest cruising. As we descend in elevation, you’ll see the changing ecosystems as we go. After the ride, you will all drive over to Oakridge, have dinner and settle in for the night.
Mileage: 30+ miles

Day 3
Grab breakfast at your hotel, we will catch a shuttle to ride Alpine Trail, perhaps Oakridge’s most famous trail. You’ll skip the long gravel road climb because we’ll drive right to the top. Depending on how everyone feels, we can add on additional trails such as Tire Mountain Trail and Cloverpatch Trail (why quit early?) After showers, we’ll walk to dinner and brews at Brewers Union Local 180, a British style ale public house and brewery.
Mileage: 18-28 miles

Day 4
Since we haven’t even scratched the surface in Oakridge, we have tons of options for the last day. We’ll see what you are up for and decide between twisty river trails, more elevation dropping descents or classic trails that wind through the dark forests. Afterwards, pile back in the van for the 2-hour drive back to Bend, ending the tour. Need more? Check out our full line up of Bend tours and Oakridge tours. We think you might want to come back for more.
Mileage: Varies