Ride Overview

The Old Cascades Crest (OCC) is one of Oregon’s most remote and untouched places to ride your mountain bike. Located in the Willamette National Forest, nestled next to the Middle Santiam Wilderness, the OCC is a 50 mile backcountry mecca just and hour from Bend. This area offers big views of Mt. Jefferson, 3 Finger Jack and the Three Sisters from the West side, a side you rarely see while mountain biking in the Willamette. We’ve navigated this area extensively and have put together an incredible three days of riding in an area few go. This is a really difficult place to ride without vehicle support, so expect daily shuttles so we can maximize our day. Don’t worry though, there will be plenty of pedaling, as this area demands an effort to reach the many peaks we’ll be ascending. Buried deep in the Cascades, expect good dirt, big descents and big climbs. This may be the finest example of the Cascades bioregion with green moss, deep loam, and high alpine lakes to cool down post ride. This trip is for ladies only; guided by, shuttled by, instructed by, and cooked by some of the most inspirational and talented ladies in the PNW. The window to ride here is short, so take advantage with us while you can!


Distance (per day)

Ascent: 2,000’
Decent: 4,000’
Estimated Mileage: 15

Distance Per Day is estimated

3 Day Trip Includes:
    • Professionally guided tour of remote single track
    • Stand Up Paddle Boarding
    • Professional YOGA instruction daily
    • Shuttles and Transportation
    • Breakfast, Lunch, and Dinner prepared by personal chef
    • Tent and Sleeping Pad
    • CLIF Bar Trail Snacks
    • Beer, Cocktails, Wine, Lacroix and other tasty beverages
    • Campfires
    • Hot Showers
Ride Date:
August 16th, 17th and 18th
3 Day Guided Trip


per person

MSR Tent with Sleeping Pad

We supply you with a two person MSR tent and Thermarest camping pad. Campground fees included. Van/RV Glamping welcomed. You’ll still need to bring a sleeping bag rated for below freezing and your pillow.

Canvas Tent with Full Size Bed

For those who want hotel amenities in the backcountry. Your tent comes fully furnished with a full size bed with a memory foam mattress, a nightstand, personal lighting and your own little room to get away. We require a minimum of 6 to make this work and the upgrade is $1000 per person.

Food and Drinks

We partner with a number of Oregon’s Top Chefs to provide you with an incredible culinary experience throughout your trip. Carnivorous , Vegetarian and Vegan menus are available. Each morning you’ll wake up to a hot or cold breakfast of your choice. Lunch and Snacks are prepared for you to take on your ride each day. After a good day of riding the bike, we’ll sit down by the table to eat a well prepared meal with each other. The menu also includes beer, cocktails and non-alcoholic beverages to quench your thirst. We want to get this right, so please let us know what you’d like to see so we can make it happen.

Sample Menu

Coffee and Tea
Cold: Yogurt, Assorted Fruit, Granola
Hot: Eggs, Bacon, Pancakes, Fruit

Sandwiches, Cookies, Snacks, Fruit

Appetizer, Main Course, Salad, sides and desert. This is a collaborative menu, so if anyone in your group has eating preferences, make sure we know about them so we can accommodate.

Driving from Portland or Seattle:

Shuttle Departure: Friday, August 16th at 10AM

Meeting Spot: Rays Food Place, Oakridge OR

Need a Ride from Portland?

Shuttle Departure: 7AM on Friday August 16 th

Meeting Spot: Meet at 5830 N Commercial Ave at 6:45 AM. You’ll be leaving your car in a safe, NE Portland neighborhood. To be safe, we recommend you leave your car empty of valuables while you’re on your trip.

Timpanogas, OR

Monday 26°FTuesday 10°FWednesday 10°FThursday 15°FFriday 23°F

The History Of The

Old Cascades Crest.

This was a huge project during the summer of 2017 to uncover some of Oregons Hidden Trail Gold. To read more about our collaboration with our community and how this ride came to be, check out this write up from Allan Cooke at Santa Cruz Bicycles.

The Old Cascade Crest was the crest of the Old Cascades around 300k years ago. The new Cascade Crest is made up of all of the volcanos we see in today’s backdrop, like Mt. Jefferson, Mt. Bacheor and Mt. Hood. Kinda cool to think this was the high point of the Cascades at one time, and now we’re riding it.

The trail system was constructed between 1930 and 1950, and was first built by the CCC and later completed by the USFS. These trails were originally created as a transportation network between fire towers; fire towers were on most peaks in the Old Cascade Crest Network. These trails were also used for animal grazing and gold mining at one point. What’s now super remote and feels really deep, once had thousands of people living there mining for gold. It’s still one of the most active hobby mining areas in the Willamette.

The network was finished as recent as the mid 90’s where the USFS connected all of these trails. The Three Pyramids, North Crescent and South Pyramid Creek Trail were all built or re-discovered in the mid 90’s, and those 3 trails make the network connected. The South Pyramid Creek Trail was an old Native American Pathway that was discovered in the process of the trails development…. you can just imagine the history in this area and how many different people have used it throughout history. It’s been dormant for the past 20 years, with very little use… and now it’s your turn to see what it’s all about.