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Obstacle Race Calendar near Winsted 2025-2026

Explore the top obstacle runs near Winsted for 2025-2026! We've gathered 25 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
26
Monday

Oh Boy 5K

5 km
June 2025
Jun
5-8
Th - Su

Ironhike Endurance Series - Spring

Trail Run 15 mi 28 mi ... 61 mi 152 mi
Jun
7
Saturday

UConn Health Half Marathon

5 km 10 km 21 km
Jun
8
Sunday

Litchfield Hills Road Race

7 mi
Jun
8
Sunday

Ironman 70.3 Western Massachusetts

Triathlon
Jun
8
Sunday

Celebrate West Hartford Fun Runs

5 km
Jun
14
Saturday

Norbrook Farm Brewery Trail Festival

Trail Run 5 km 10 km 4 hr
Jun
14
Saturday

Pat Griskus Olympic Triathlon

Triathlon
Jun
26
Thursday

Riverfront Hartford 5K

5 km
July 2025
Jul
5
Saturday

Litchfield Hills Triathlon

Triathlon
Jul
12
Saturday

Move With the Urban League

5 km
Jul
12
Saturday

Hopkins Vineyard Triathlon

Triathlon
Jul
24
Thursday

Riverfront Hartford 4 Mile

4 mi
Jul
26
Saturday

Valley of Hartford 5K

5 km
August 2025
Aug
2
Saturday

The People's Forest 7-Mile Trail Run

Trail Run
Aug
9
Saturday

Mentoring Matters 5K

5 km
Aug
17
Sunday

Old Wethersfield 10K

5 km 10 km
Aug
21
Thursday

Riverfront East Hartford 5 Mile

5 mi
Aug
23
Saturday

Jug End Loop Ultra

Trail Run 4 mi
Aug
23
Saturday

DK Movement Cares 5K

5 km
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