Lexington

Trail Running Calendar near Lexington 2026-2027

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.

November 2026

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.

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.

Chessie Trail Marathon

Trail Run 5 km 10 km 13 mi 26 mi

Trail marathon, half, 10K, 5K and relay on the Chessie Nature Trail in Virginia with USATF certified courses and a virtual option.

Trail marathon, half, 10K, 5K and relay on the Chessie Nature Trail in Virginia with USATF certified courses and a virtual option.

Mountain Masochist Trail Run 50 Miler

Montebello | 17 mi from Lexington

Trail Run 50 km 50 mi 100 km

A fall ultramarathon in Montebello VA on Nov 7 2026 offering 100K, 50 Miler and 50K courses through Blue Ridge single track and forest roads.

A fall ultramarathon in Montebello VA on Nov 7 2026 offering 100K, 50 Miler and 50K courses through Blue Ridge single track and forest roads.

March 2027

Bel Monte Endurance Races

Stuarts Draft | 28 mi from Lexington

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.

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.

Terrapin Mountain

Big Island | 18 mi from Lexington

Trail Run Half Marathon 50 km

March 20, 2027 in Sedalia, VA: a trail 50k and half-marathon around Terrapin Mountain and nearby ridges, organized by Winding Way Run Co.

March 20, 2027 in Sedalia, VA: a trail 50k and half-marathon around Terrapin Mountain and nearby ridges, organized by Winding Way Run Co.

September 2027

Odyssey Trail Running Rampage

Millboro | 15 mi from Lexington

Trail Run 6 mi 13 mi 26 mi 50 km

Trail race weekend at Douthat State Park offering 50K, 26, 13 and 6 mile loop courses with significant elevation and stocked aid stations.

Trail race weekend at Douthat State Park offering 50K, 26, 13 and 6 mile loop courses with significant elevation and stocked aid stations.