Oregon Trail Gravel Grinder

June 21 - June 25 2023
Sisters, Oregon, USA
Date Confirmed
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Distances: 365 miles
Difficulty: Difficult terrain with longer, steeper hills
Limited to: 400 Participants

Across the red cinder roads of Oregon’s remote high desert country, over the dramatic Cascade Mountains, through dank moss-covered rainforests and along historic wagon trails where settlers once tested their grit on the journey west, the Oregon Trail Gravel Grinder promises nothing less than the adventure of a lifetime.

The event, is the creation of Breakaway Promotions, one of the country’s most seasoned cycling production companies. It will start and finish in the character-rich saddle town of Sisters and will pass through 365 miles of Oregon’s most scenic and applause-worthy gravel roads, with fully-supported fireside campouts and entertainment to rest and refuel each night.

True to its name, the Oregon Trail Gravel Grinder will have a decidedly-playful western theme- think Daniel Boone hats and wagon wheel medals, covered wagon aid stations, boot-stomping ale and entertainment at night and strong cowboy coffee in the morning. Each stage will even have a shorter “Settler Route” for folks to saddle sore for the full ride and want to make it to camp before the biscuits start burning.

Oregon Trail Gravel Grinder


Start Located At: 171 S Elm St Sisters, OR 97759 USA
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5 days of the greatest gravel in the PNW!  Your fully-supported all-inclusive gravel bike vacation!

Day 1- Sisters to Blue Ridge/McKenzie 

Day 2- Blue Ridge/McKenzie to Oakridge

Day 3- Oakridge to Oakridge

Day 4- Oakridge to La Pine

Day 5- La Pine to Sisters


Registration Fees



2 Custom Event Shirts (because you should change your shirt at least twice during this event)
1 Pair of Socks
Meal Package prepared by the outstanding Spin Catering
4 breakfasts
5 lunches
5 dinners
NOTE: vegan options are available
Nightly Beer token & Whiskey Tasting
Nightly Games
Nightly Live Music
Impressive Finishers Medal
Finishers Pint Glass
Nightly camping locations on grass
Showers and restrooms are available each day
Chip timing with nightly online results
Gear transport so that you don't have to haul your own camping gear (unless elected)
Well Stocked Aid Stations
Mechanical Support
Awesome SWAG Bag!

Prize / Race Categories

Prize money available to the Explorer category only. Finishers medals and finishers commemorative pint glasses for everyone.

Adequate Car Parking
Free Parking
Changing Rooms
Pre-Packet Pickups
Support for Participants
Route Signposted
First Aid
Emergency Contact No
Roving Mechanical Support
Mechanical Support at Rest Stops
Course Timing
KOM/QOM Competition
Category / Race Prizes
Finishing Medals
Results Within 24 Hours
Post Ride Shower
Finish Line Chute
Feed / Aid Stations
Pre Event Meal(s) Provided As Part of Entry
Post Event Meal(s) Provided As Part of Entry