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Obstacle Race Calendar near Brookfield 2025-2026

Explore the top obstacle runs near Brookfield for 2025-2026! We've gathered 95 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
6
Saturday

Santa Made Me Do It

2 mi 5 km
Dec
6
Saturday

Nia Jingle Bell Run

5 km
Dec
7
Sunday

Christopher Martin's Christmas Run

5 km
Dec
7
Sunday

Feeding 500 Holiday Hustle

5 km
Dec
13
Saturday

Frosty Forest 5K

Trail Run 5 km
Dec
13
Saturday

Norwalk Jingle Bell 5K

5 km
Dec
13
Saturday

BPT PAL Christmas Village Road Race

3 mi
Dec
14
Sunday

Taco Trials

Trail Run 10 mi
Dec
14
Sunday

The Holiday Run & Walk for Toys

5 km
Dec
28
Sunday

The West Rock Winter Fat Ass Extravaganza

Backyard Ultra 2 mi
January 2026
Jan
1
Thursday

Brookfield Lions Run for Sight

4 mi
Jan
1
Thursday

Chilly Chili Run - Woodbridge

2 mi 5 km
Jan
4
Sunday

MADD Dry 5K

5 km
February 2026
Feb
8
Sunday

IRIS Run for Refugees

5 km
Feb
22
Sunday

Lake Waramaug Polar Bear Run

8 mi
March 2026
Mar
1
Sunday

ShamRock & Roll 5K

5 km
Mar
21
Saturday

Enchanted Forest Ultra Run

Backyard Ultra 50 km
Mar
28
Saturday

Savin Rock Marathon

Half Marathon Marathon
Mar
29
Sunday

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
April 2026
Apr
12
Sunday

Millbrook Marathon

26 mi
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