Chessie Trail Marathon, Half Marathon, 10K, 5K, & 26.2 Relay
South River, Virginia, United States
Nov 7, 2026 - Saturday
5k, 10k, Half-marathon, Marathon
Race Information
Run The Chessie! Run America’s most spectacular rail trail! The seven-mile Chessie Trail, situated at the southern end of the Shenandoah Valley, parallels the scenic Maury River and connects historic Lexington, Virginia, with the boom-town community of Buena Vista. The smooth, flat, gravel and grass trail runs along the former Chesapeake and Ohio rail lines and parts of the earlier James and Kanawha Canal towpath.
You’ll run through an ever-changing landscape along the wild Maury River, through farmland and leafy canopies at their peak of fall color, past ruins of massive stone locks and dams. View wildlife from fish and ducks to rabbits, wild turkeys, river otters, and even bald eagles.
Related Events
James River Scramble
Date: May 16, 2026 - Saturday
Size: 500 - 1,000 participants
Location: Richmond, Virginia
Corporate FunRun Northern Virginia 5k
Date: May 27, 2026 - Wednesday
Size: 100 - 500 participants
Location: Herndon, Virginia
New River Trail Races
Date: Apr 11, 2026 - Saturday
Size: 100 - 500 participants
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👍 Run Pick of the Month: Frederick Running Festival
📍Frederick Fairgrounds - Frederick, MD - May 2 & 3, 2026
💸 Exclusive $15 Off! Use Code: Run26Guide
Why We Like This Run:
✅ Free Parking, Free Beer & Live Music
✅ Fun, Flat & Scenic Course
✅ Run Both Days for Added SWAG
Get It All at the Frederick Running Festival. A longtime community favorite of more than 20 years and just outside Washington, D.C., the Frederick Running Festival delivers big-race energy with small-town charm. With four race options finishing at the Frederick Fairgrounds, this weekend is built for runners who want the full experience.
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Race Facts
Race Size: 100 - 500
Elevation: Fast and Flat
Course Type: Trail
Boston Qualifier: Yes
Kids Run: No
Where to Stay
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