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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
12
Sa

Odyssey Trail Running Rampage

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

Trail Run 4 mi 9 mi
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.
November 2026
Nov
7
Sa

UltraTrax Wintergreen

Trail Run Walk 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 Walk 5 km 10 km 13 mi 26 mi
USATF certified trail races on the Chessie Nature Trail near Lexington VA offering Marathon, Half, 10K, 5K and a 26.2 relay plus virtual options.
Nov
7
Sa

Mountain Masochist Trail Run 50 Miler

Trail Run 50 km 50 mi 100 km
November trail ultramarathon in Montebello VA offering 100K, 50 Miler and 50K over single track, dirt and logging roads through the Blue Ridge.
March 2027
Mar
20
Sa

Bel Monte Endurance Races

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.
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