Chessie Trail Marathon, Half Marathon, 10K, 5K, & Marathon Relay

Chessie Trail Marathon, Half Marathon, 10K, 5K, & Marathon Relay starts in Lexington on November 7, 2026, with every distance going off at 8 a.m. — the marathon (26.2 miles), a marathon relay, the half marathon (13.1 miles), the 10K and the 5K. The races follow the Chessie Nature Trail, a well-kept gravel and grass path along the Maury River that links Lexington and Buena Vista in the Shenandoah Valley.

There are no road crossings, and the route passes varied scenery, wildlife and historic remnants, with volunteers staffing the way. Courses are certified and the event is USATF-sanctioned, so a Boston qualifying attempt is on the table here. Build for 16 weeks with a weekly long run, and spend some of it on unpaved ground: gravel and grass ask a little more of your legs than asphalt does over 26.2 miles.