Massachusetts Obstacle Race Calendar 2025-2026

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Explore the best obstacle runs in Massachusetts for 2025-2026! Our updated list features 257 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

May 2026
May
9
Saturday

Grafton Gazebo Road Race

5 km
May
9
Saturday

Barns & Blooms Half Marathon

13 mi
May
9
Saturday

Enjoy Your Life Happy Half Marathon

5 km 21 km
May
16
Saturday

Runnin' for a Cause, Not from the Cops

5 km
May
17
Sunday

Harpoon 5-Miler

5 mi
May
17
Sunday

Evan's Run

5 km
May
30
Saturday

Wildcat 5K Trail Run-Walk-Wag

Trail Run 5 km
June 2026
Jun
7
Sunday

Ironman 70.3 Western Massachusetts

Triathlon
Jun
7
Sunday

Twin Lobster Half Marathon

13 mi
Jun
7
Sunday

Black Hat Brew 5k

5 km
Jun
14
Sunday

Battle of Bunker Hill 5K Road Race

5 km
Jun
27-28
Sa - Su

New England Spartan Event Weekend

Obstacle Run 5 km 10 km 4 hr
July 2026
Jul
4
Saturday

Leonide J. Lemire Road Race 4.9 Mile Run

5 mi
Jul
25
Saturday

Dennis Road Race

3 mi 5 mi
August 2026
Aug
1
Saturday

Savage Race - Boston

Obstacle Run 3 mi 7 mi
Aug
2
Sunday

Greenfield Triathlon

Triathlon
Aug
16
Sunday

Falmouth Road Race

7 mi
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