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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.

June 2025
Jun
5-8
Th - Su

Ironhike Endurance Series - Spring

Trail Run 15 mi 28 mi ... 61 mi 152 mi
Jun
14
Saturday

Norbrook Farm Brewery Trail Festival

Trail Run 5 km 10 km 4 hr
Jun
21
Saturday

Free to Run Trail Races

Trail Run 15 km 25 km 50 km
Jun
22
Sunday

Stissing Triathlon

Triathlon
July 2025
Jul
5
Saturday

Litchfield Hills Triathlon

Triathlon
Jul
11-14
Fr - Mo

Notchview Ultra

Trail Run 6 hr 12 hr ... 48 hr 72 hr
August 2025
Aug
2
Saturday

The People's Forest 7-Mile Trail Run

Trail Run 7 mi
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 13 mi 8 hr
October 2025
Oct
2-5
Th - Su

IronHike Endurance Series

Trail Run 15 mi 28 mi ... 61 mi 152 mi
Oct
11
Saturday

Hartland Harvest Run

3 km 5 km
Oct
12
Sunday

Mohawk Mountain Race

Trail Run 5 km 10 km 13 mi 26 mi
Oct
18
Saturday

The Little Guild Run & Wag 5K

5 km
December 2025
Dec
13
Saturday

North Canaan Santa Chase 5K

5 km
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