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Trail Running Calendar near Westfield 2025-2026

Explore the top trail runs near Westfield for 2025-2026! We've gathered 57 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
25
Saturday

Book It for Books 10k

Trail Run 5 km 10 km
Oct
25
Saturday

Collinsville Trick or Trot

5 km
Oct
25
Saturday

The Ludlow Clocktower Classic 5k

5 km
Oct
26
Sunday

Monson Memorial Classic Half Marathon

5 km 21 km
November 2025
Nov
1
Saturday

Robert Tedford Memorial Road Race

5 km
Nov
2
Sunday

Western Mass 10

5 km 10 mi
Nov
8
Saturday

East Windsor Veterans Day 5K

5 km
Nov
9
Sunday

GySgt. Thomas J. Sullivan Remembrance Run & Walk

2 mi 5 km
Nov
22
Saturday

Roadtown Turkey Trot

5 km
Nov
23
Sunday

Cleats On The Streets

5 km
Nov
27
Thursday

Manchester Road Race

5 mi
December 2025
Dec
7
Sunday

Cla Blue Back Mitten Run

5 km
Dec
13
Saturday

Santa Shuffle - Longmeadow

5 km
January 2026
Jan
11
Sunday

HTC Winter Series Barkhamsted 17 Mile

9 mi 17 mi
May 2026
May
3
Sunday

Runway 5k - Northampton

5 km
June 2026
Jun
7
Sunday

Ironman 70.3 Western Massachusetts

Triathlon
July 2026
Jul
11
Saturday

Litchfield Hills Triathlon

Triathlon
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