The Trail

JULY 8 - 12, 2026 BEND, OR

Oregon Trail is one of the most complex and challenging gravel events in North America to produce, covering 350 miles of Oregon’s scenic and wild backcountry gravel roads. It is our mission at Team Breakaway, to make the logistics for each and every rider easy so that they can focus on nothing more than pedaling some of the most amazing gravel roads in North America for 5 days straight!

NO AERO BARS are allowed on ANY stage of the

Oregon Gravel Grinder series.

Route Information: Two distances are offered, Pioneer and Settler. The Pioneer category is for racers and has nightly and overall podiums. The Settler category is a non-competitive, bike tour challenge ride.

Pioneer- approximately 350 miles, 30,000 feet climbing*. Pioneers will ride approximately 50 to 80 miles per day with 4,500 to 7,000 feet of climbing.

Settler- approximately 250 miles, 15,000 feet climbing*. Settlers will ride approximately 30 to 65 miles per day with 2,000 to 5,250 feet of climbing.

*Current route information is an estimation based on the previous year’s routes and current route plan. Distances and climbing may be altered slightly due to snow on the course and road conditions after the winter season.

Surface: 60% - 100% gravel each day

Aid Stations: We pride ourselves in the legitimate high-quality of the aid stations. Well-stocked aid stations will be located roughly every 20 to 25 miles along the courses. There will be a variety of foods such as Granola Bars, Bananas, Apple Sauce, Bananas, Oranges, GU, Water, GU Hydration, Rice Krispie Treats, and some other tasty snacks.

In addition to food, we will also have extra tubes tire pumps, and tires. Aid Stations will be staffed with experienced mechanics and aid station expert leads, as well as local volunteer youth groups, who work hard to make sure your needs are met. In addition to the assortment of fuel and snacks, the new Breakaway Revolutionary Water Wagon, a game-changer for super-speed water dispensing, will ensure your hydration station time is minimal.

Schedule: July 8-12, 2026

Tuesday, July 7th- Packet Pickup- Bend, Oregon
Wednesday, July 8th- RIDE DAY 1, Bend to McKenzie
Thursday, July 9th- RIDE DAY 2, McKenzie to Oakridge
Friday, July 10th- RIDE DAY 3, Oakridge Time Trial (uphill and downhill course time trial)
Saturday, July 11th- RIDE DAY 4, Oakridge to Gilchrist
Sunday, July 12th- RIDE DAY 5, Gilchrist to Bend

Daily Schedule Outline-

The schedule may change each day based on course, weather, etc. Riders will be notified as soon as changes are made.

Gear Tote Drop Off- 6:30 - 8:30 am- Riders are required to drop off their gear tote to our transportation team each morning. The team will then move their gear to the day’s final camping spot.
Breakfast- For days 2 and 3, breakfast is served from 6:30 - 8:30 am. For days 4 and 5, breakfast is served from 6:00 - 7:30 am.
Ride Start- For days 1, 2, and 3 the ride start will be at 9 am. For days 4 and 5, the ride start will be 8 am.
Snack Shack (lunch)- The Snack Shack will open at 12:00 pm each day.
Dinner Buffet- 5:00 - 8:00 pm
Oregon Trail Castelli Saloon, Beer & Whiskey Bar- 5:00 - 9:00 pm
Awards, Games, Celebrations, & Entertainment- each evening at camp

Trail Day 1 - Wednesday
Start: Bend
Finish: McKenzie

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Trail Day 2 - Thursday
Start: McKenzie
Finish: Oakridge

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Trail Day 3 - Friday
Start: Oakridge
Finish: Oakridge

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Trail Day 3 - Friday
Start: Oakridge
Finish: Oakridge

Our classic Stage 3 Enduro Day returns in 2026. Riders will roll east from Oakridge on Hwy 58 before turning onto Kitson Ridge Road to begin three timed segments:

Segment 1: A 6.5-mile uphill time trial climbing 2,100 feet - low-angle power climbing with no steep pitches (false hope for the non-climbers!).
Segment 2: The "Roller Coaster" - a 6-mile segment full of twists, dips, and turns under a thick tree canopy, ending at the same elevation it begins.
Segment 3: The grand finale: 4 miles of pure downhill, dropping over 1,500 feet with zero straightaways and non-stop flow.