Trail Running Calendar near Lexington 2026-2027

September 2026

Trail Run 6 mi 13 mi 26 mi 50 km

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.

Sep

19

Sa

Nasty 9 Trail Run

Lexington

Trail Run 4 mi 9 mi

Trail races at Brushy Hills near Lexington, VA offering 9 mile and 4 mile single track courses with significant climb; proceeds support local conservation and school teams.

November 2026

Nov

7

Sa

UltraTrax Wintergreen

Roseland | 25 mi from Lexington

Trail Run 7 mi 14 mi 21 mi 28 mi

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.

Nov

7

Sa

Chessie Trail Marathon

Lexington

Trail Run 5 km 10 km 13 mi 26 mi

Trail races on the Chessie Nature Trail near Lexington VA, featuring marathon, half, 10K, 5K and a relay on a smooth gravel and grass course with aid stations and medals.

Nov

7

Sa

Mountain Masochist Trail Run 50 Miler

Montebello | 17 mi from Lexington

Trail Run 50 km 50 mi 100 km

Mountain Masochist Trail Run in Montebello VA offers 100K, 50 Miler and 50K routes through Blue Ridge single track and forest roads with site specific camping available.

March 2027

Mar

20

Sa

Bel Monte Endurance Races

Stuarts Draft | 28 mi from Lexington

Trail Run 25 km 50 km 50 mi

A spring mountain trail event in the Blue Ridge Mountains on March 20, 2027, offering 50 mile, 50k and 25k races on mostly single track and forest roads, with limited entries and cabins at the start finish.