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Trail Running Calendar near Brattleboro 2025-2026

Explore the top trail runs near Brattleboro for 2025-2026! We've gathered 13 exciting races in the area. Check out our detailed list below to find your next local race.

July 2025
Jul
4
Friday

Running of the Bears - Stratton Mountain

5 km
Jul
4
Friday

Firecracker 4-Miler - Brattleboro

4 mi
August 2025
Aug
9
Saturday

Lover's Lane - Chester, VT

Trail Run 6 hr 12 hr
Aug
24
Sunday

New England Green River Marathon

42 km
Aug
31
Sunday

Swanzey Covered Bridges Half-Marathon

13 mi
September 2025
Sep
14
Sunday

Pisgah Mountain Trail Races

Trail Run 23 km 50 km
Sep
14
Sunday

Tree House Brewing Company Half Marathon

13 mi
Sep
28
Sunday

Clarence DeMar Marathon

13 mi 26 mi
October 2025
Oct
5
Sunday

Covered Bridge Classic

10 km
November 2025
Nov
1
Saturday

MDS Run~Walk~Smile

10 km
Nov
8
Saturday

Orange Turkey Trot

5 km
Nov
8
Saturday

Race for DFL

Trail Run 4 mi 50 mi
Nov
22
Saturday

Roadtown Turkey Trot

5 km
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