Last updated July 22, 2024--

The Oregon Trail Gravel Grinder is the third leg of the Oregon Gravel Grinder Series; this "Grand Tour of Gravel" is a five-day event that will challenge and reward racers and adventure riders alike, not only on the epic days in the saddle but the celebration of the gravel tribe each night at camp.   This unique experience offers a fully supported race-vacation experience covering approximately 350 miles and 25,000-33,000 feet of elevation gain over mixed terrain through the Cascade Mountain Range in five days and four nights. Strambecco rates the Oregon Trail Gravel Grinder as one of the Best Gravel Cycling Race Events in the Northwest and the Best Gravel Cycling Race Events in the Oregon.

Below you will find information on course details, lodging, dining, and other outdoor activities while visiting Sisters, OR.

Event & Course Info

There are two different rider-type classifications for this event: either difficult rides for each day or you can register as Pioneer or Settler. Pioneers usually ride up to 10 miles more and climb 500-1000 feet more daily than the Settler.

Pioneer Route: Approximately 350 miles with 30,000 feet of climbing, ~5,000 miles per day.
Settler Route: Approximately 250 miles with 15,000 feet of climbing, ~3,000 miles per day.

Each night, the riders are celebrated at various campsites. Event registration includes all support, tents, food, and nightly entertainment. There are even professional massages available for participants. The event starts and ends in Sisters, OR, a full loop through the Cascades, where each day has difficulty classified as Moderate, Hard, or Very Hard. Aid stations along the way keep all riders fueled and hydrated for hundreds of miles. This event is for you if you want a great multi-day cycling experience.

Below is a high-level indication of each stage, but it does not represent the actual 2025 route, which has not been announced:

Day 1: Bend to Gilchrist
- Distance: 66.3 miles
- Elevation Gain: 3336 feet
- Road Surface: 60% Gravel 40% Paved
- Highlights: Starting in Bend, riders navigate through picturesque terrain, including forested areas and scenic byways.

Day 2: Gilchrist to Oakridge
- Distance: 92 miles
- Elevation Gain: Significant climbs (4,700 ft total), including remote gravel roads
- Road Surface: 78% Gravel 22% Paved
- Highlights: Challenging ascents and descents with breathtaking views of the Cascades.

Day 3: Oakridge Time Trial
- Distance: 30.5 miles
- Elevation Gain: 3,000 ft of climbing
- Road Surface: 54% gravel 40% paved 6% singletrack
- Features: Multiple racing segments, testing speed and endurance on varied terrain.

Day 4: Oakridge to McKenzie
- Distance: 83.1 miles
- Elevation Gain: Substantial climbing, 9,000ft+
- Road Surface: 70% gravel 30% paved
- Highlights: Diverse landscapes from dense forests to open vistas, including long gravel stretches.

Day 5: McKenzie to Bend
- Distance: 79.7 miles
- Elevation Gain: nearly 8,000 ft
- Road Surface: 78% Gravel 22% Paved
- Highlights: Final push back to Bend, featuring a mix of gravel and paved sections with panoramic views.

Participants in the Pioneer and Settler routes experience a mix of challenging climbs, technical descents, and stunning Oregon landscapes, making for an adventurous and rigorous five-day gravel ride. They also enjoy well stocked aid stations, nightly campouts, gourmet food, professional support, and entertainment.

It is highly suggested that riders take the extra 3/4 miles from the timing finish and head up to the lake to dip their legs in the cool lake water and take in the scenery before rolling to the finish on the fast descent back into Sisters, Oregon, where the post-race festivities begin.

Area Accommodations & Things to Do

Sisters, OR is a vibrant hub for outdoor athletes and enthusiasts, offering a diverse array of adventures set against the stunning backdrop of the Cascade Mountains. This charming town is a gateway to an abundance of recreational activities, including hiking, mountain biking, and trail running through picturesque landscapes. The nearby Three Sisters Wilderness boasts miles of trails with breathtaking vistas, pristine alpine lakes, and challenging terrain. In winter, the region transforms into a playground for cross-country skiing and snowshoeing. With its blend of natural beauty, small-town charm, and a thriving outdoor culture, Sisters is a must-visit destination for those seeking adventure and exploration in the Pacific Northwest.

Where to Stay in Sisters

Sisters, Oregon, features a variety of accommodation options that capture the essence of the Pacific Northwest, from rustic cabins and cozy bed and breakfasts to luxury resorts and boutique hotels. These lodgings cater to a range of preferences, offering guests a chance to enjoy the area’s natural beauty and charm, whether nestled in the forest or right in the heart of this quaint town. There is no official lodging partner for the Oregon Trail Gravel Grinder but hotel options include The Cottage Inn, FivePine Lodge & Spa, the Suttle Lodge and Boathouse, Five Pine Lodge & Cabins (whose owners are the event sponsors!), and Sisters Inn & Suites. If you enjoy a more home-like experience, there are some great vacation rentals that will suit a variety of needs. For those who appreciate the simplicity of sleeping under the stars, check out Creekside Campground or one of the many one-of-a-kind camping options available in the surrounding area.

Dining in Sisters

Sisters, Oregon, offers a charming culinary scene that mirrors its rustic, Western-themed ambiance. This small town features a selection of cozy cafes, local bakeries, and family-owned restaurants serving everything from gourmet meals to classic comfort foods, often showcasing regional ingredients and craft beverages from the Pacific Northwest. In addition to the event celebration gatherings, Sisters, Oregon, has a quaint downtown with many retail shops and restaurants, including Sisters Depot, The Kitchen Table, and Sisters Saloon. Local favorites include Sisters Bakery, Sisters Coffee Company, and Open Door.

Outdoor Activities Around Sisters

Sisters, Oregon, nestled at the base of the Cascade Mountains, transforms into an outdoor playground each year, offering athletes a variety of activities amid stunning natural scenery. With the snow beginning to melt and wildflowers in bloom, this charming town provides the perfect setting for adventurers and sports enthusiasts. Just a short drive from Sisters, Smith Rock State Park is renowned for its dramatic rock formations and scenic river canyons. It is an ideal destination for hiking enthusiasts looking for a challenging day out. The park offers several trails ranging from easy walks along the Crooked River to the more strenuous Misery Ridge Trail, which rewards hikers with panoramic views of the central Oregon landscape and the snow-capped peaks of the Cascades. The Peterson Ridge Trail system, directly accessible from Sisters, is a paradise for mountain bikers. With over 30 miles of trails tailored to various skill levels, riders can enjoy everything from gentle loops to technical descents. In spring, the weather is typically mild, making it an excellent time for athletes to experience the trail’s diverse terrain and vibrant spring vegetation. For water sports enthusiasts, Suttle Lake offers a serene yet active getaway. Located in the Deschutes National Forest, this natural lake provides clear, calm waters ideal for kayaking. Paddlers can enjoy peaceful hours exploring the lake’s perimeter, taking in views of the surrounding forest and volcanic peaks. The lake’s accessibility and the presence of rental facilities nearby make it a convenient choice for a day on the water.

Related Events

The Oregon Trail Stage Race is part of the Oregon Gravel Grinder Series produced by Breakaway Promotions, which operates several other top single-day and multi-day gravel events.   The full event line-up includes Gorge;  Cascade, Oregon Trail; and Ochoco. There are discounts when riders register for three or four at a time. For all multi-day riders, this is your chance to experience some of the best gravel rides Cascade Mountain Range and the national parks of Oregon have to offer in the spring and summer.

Multi-sport athletes looking for other premier races and events in Oregon and the broader Northwest region can take a peek at all of our related Strambecco Best rated event guides:

• Best Gravel Cycling Race Events in the Northwest
• Best Road Cycling Race Events in the Northwest
• Best Trail Running Race Events in the Northwest
• Best Mountain Bike Race Events in the Northwest
• Best Cycling Race Events in Oregon

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