Chessie Trail Marathon

Lexington, United States • 7 Nov 2026

Chessie Trail Marathon and Distance Events : November 7, 2026

The event takes place on the Chessie Nature Trail in the southern Shenandoah Valley, a seven-mile rail-trail that runs alongside the Maury River between Lexington, Virginia, and Buena Vista. The trail surface is smooth gravel and grass, generally about 10 feet wide, with a very gentle grade. Runners follow sections of former rail line and canal towpath and remain on the trail without road crossings for the full marathon distance.

Distances offered:

  • Marathon (26.2 miles) out-and-back loops covering the full route twice
  • Half Marathon out-and-back route using most of the trail
  • 10K out-and-back with a final downhill finish
  • 5K out-and-back through river bends and cliffs
  • 26.2 Relay four legs roughly 8.5m, 4.6m, 8.5m, 4.6m

All four courses are USATF certified and the marathon is a Boston Qualifier. Aid stations provide water, Gatorade, fruit and snacks at the start/finish, turnarounds and near the South River bridge; refill stations for reusable containers are available. Amenities vary by distance and include chip timing, custom shirts, finisher medals, drop bag service, porta-potties, free parking near the start, and post-race food such as pizza and pancakes. A virtual option is offered for the marathon, half, 10K and 5K with mailed amenities and self-reporting of results. Registration is handled online; transfers and deferrals are allowed through October 31, 2026, and refunds are not offered.

The trail can present natural hazards such as overhanging branches, loose rocks, springs, occasional livestock presence and small roots, so participants are asked to watch footing and follow posted trail etiquette. Visit the organization's website for the most recent information.

Race information

26 mi
26.2 Relay
26 mi
Marathon
13 mi
Half Marathon
10 km
10k
5 km
Visit the organization's website for the most recent information.
Trail runs nearby

Trail races at Douthat State Park featuring a roughly 13-mile loop used for a 50K, marathon, half marathon, and a six-mile race, with multiple aid stations, loop-based finisher rules, and limited field sizes.

Trail race at Brushy Hills near Lexington VA offering a 9 mile route with 2000 ft gain and a 4 mile option; proceeds support local trails and school teams.

A timed, non competitive trail event at Wintergreen offering 7, 14, 21 and 28 mile loop options. Participants can add weighted vests, face a 10 hour cutoff for awards, and expect on site parking and finisher items.

November trail ultramarathon in Montebello VA offering 100K, 50 Miler and 50K over single track, dirt and logging roads through the Blue Ridge.

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