Trail Running Calendar near Stuarts Draft 2026-2027

October 2026

Trail Run 3 mi 10 km

Fundraising trail event in Crozet with 5K, 10K and a 0.75 miles family run, limited fields, race shirts, pancakes and a post-race trails fest.

November 2026

Nov

7

Sa

UltraTrax Wintergreen

Roseland | 20 mi from Stuarts Draft

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 | 28 mi from Stuarts Draft

Trail Run 5 km 10 km 13 mi 26 mi

November 7, 2026 races on the Chessie Nature Trail in Virginia including marathon, half, 10K, 5K and a 26.2 relay on a flat gravel and grass rail trail.

Nov

7

Sa

Mountain Masochist Trail Run 50 Miler

Montebello | 13 mi from Stuarts Draft

Trail Run 50 km 50 mi 100 km

Trail races of 100K, 50 mile and 50K in Montebello VA following mountain single track and forest roads through peak fall foliage.

Nov

8

Su

Harvest Hustle 10k - North Garden

North Garden | 22 mi from Stuarts Draft

Trail Run 5 km 10 km

Trail 5k and 10k at Walnut Creek Park with chip timing, medals, water stations, awards by age group, and a virtual option.

March 2027

Mar

20

Sa

Bel Monte Endurance Races

Stuarts Draft

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.

August 2027

Aug

14

Sa

Martha Moats Baker

Mount Solon | 21 mi from Stuarts Draft

Trail Run 31 mi 39 mi

A limited-field trail ultrarun in Jefferson National Forest offering a roughly 60 km course with a 50 km Party Route, three aid stations, and required self-sufficiency.