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Trail Running Calendar near Lexington 2026-2027

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Explore the top trail runs near Lexington for 2026-2027! We've gathered 6 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
19
Sa

Nasty 9 Trail Run

Trail Run 4 mi 9 mi
Trail races at Brushy Hills near Lexington VA with 9 mile and 4 mile single track courses, notable elevation gain, and proceeds supporting local schools and conservation.
November 2026
Nov
7
Sa

UltraTrax Wintergreen

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

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

Trail Run 50 km 50 mi 100 km
Trail races in Montebello on November 7 with 100K, 50 Miler and 50K routes that focus on single track and forest roads.
March 2027
Mar
20
Sa

Bel Monte Endurance Races

Trail Run UTMB 20K/50K/100K 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.
Mar
20
Sa

Terrapin Mountain

Trail Run Half Marathon 50 km
Experience the 20th anniversary of the Terrapin Mountain 50k and Half Marathon featuring the beautiful trails of the Blue Ridge Mountains in Sedalia Virginia
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