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THE TRAIL
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.
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Pioneer- approximately 335 miles, 31,000 feet climbing*.
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Settler- approximately 255 miles, 21,000 feet climbing*.
*Current route information is an estimate 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
SEE FULL GPS COURSE FILES, DAILY MILEAGE, AND ELEVATION HERE
Stage 1: Sisters to McKenzie
In 2026, Oregon Trail Gravel returns to its roots, once again starting in Sisters and traveling counterclockwise around the Oregon Cascade Range. The bad news? The legendary Santiam Sandbox is back. The good news? You'll tackle it early in Stage 1, when legs are fresh, spirits are high, and optimism is still abundant.
At mile 22.5 for Pioneers and mile 14.5 for Settlers, riders enter the original section of the Historic Santiam Wagon Road. Built in the early 1860s to connect Central Oregon with the Willamette Valley, this route was originally designed for oxen and wagons—not gravel bikes. The road cuts through deep volcanic ash and pumice, creating eight miles of riding, pushing, and problem-solving that have become a hallmark of the Oregon Trail experience.
By the time riders reach the Sandbox, the field will already be well spread out. Because this section is primarily uphill, the first 6.5 miles present relatively low risk despite the challenging surface. The final 1.5 miles, however, deliver the true Santiam experience: deep sand combined with sharp volcanic rock embedded in the roadbed, creating a memorable one-two punch before reaching smoother terrain.
At mile 30.7 for Pioneers and mile 22.8 for Settlers, riders emerge from the historic wagon road onto traditional Forest Service roads. Here, the landscape transforms dramatically as the High Desert gives way to lush forests and towering evergreens. The reward is immediate—a long descent toward the Willamette Valley on some of the smoothest and most enjoyable gravel roads in the Pacific Northwest.
For Settlers, only a handful of short climbs remain before a mostly downhill run into Blue River. Pioneers, however, still have one significant climb ahead before Aid Station 3, where opportunities await to collect Crown of the Mountain points or launch a decisive move for the stage victory.
With more than 2,000 feet of net elevation loss and smooth, fast roads making up nearly 60% of the route, Stage 1 is designed to be quick, exciting, and an unforgettable way to begin your Oregon Trail journey.
Pro Tip: The McKenzie River is just a stone's throw from our Day 1 campsite. Walk out the back gate of the McKenzie Community Track and carefully cross Highway 126 to reach the boat ramp. It's the perfect place to rinse off the dust, cool your legs, and soak in the icy waters of one of Oregon's most beautiful rivers after an epic first day on the trail.