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Obstacle Race Calendar near Great Barrington 2025-2026

Explore the top obstacle runs near Great Barrington for 2025-2026! We've gathered 15 exciting races in the area. Check out our detailed list below to find your next local race.

August 2025
Aug
9
Saturday

Sweltering Summer Ultra

Trail Run 8 hr
Aug
23
Saturday

Jug End Loop Ultra

Trail Run 4 mi 6 hr
September 2025
Sep
21
Sunday

Angevine Farm Trail Festival

Trail Run 5 km 21 km 8 hr
Sep
27
Saturday

Hogsback Half Marathon

13 mi
October 2025
Oct
2-5
Th - Su

IronHike Endurance Series

Trail Run 15 mi 28 mi ... 100 mi 152 mi
Oct
5
Sunday

Norfolk Land Trust Trail Race Series

Trail Run 5 km 10 km 13 mi
Oct
11
Saturday

Hartland Harvest Run

3 km 5 km
Oct
12
Sunday

Mohawk Mountain Race

Trail Run 5 km 10 km 21 km 42 km
Oct
18
Saturday

The Little Guild Run & Wag 5K

5 km
Oct
19
Sunday

Veeder Tree Farm 5K

Trail Run 3 km 5 km 10 km
December 2025
Dec
13
Saturday

North Canaan Santa Chase 5K

5 km
January 2026
Jan
11
Sunday

HTC Winter Series Barkhamsted 17 Mile

8 mi 17 mi
April 2026
Apr
25
Saturday

Shane Kinsella Memorial Run/Walk

2 mi 5 mi
June 2026
Jun
28
Sunday

Stissing Triathlon

Triathlon
July 2026
Jul
11
Saturday

Litchfield Hills Triathlon

Triathlon
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