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Trail Running Calendar near Fitzwilliam 2025-2026

Explore the top trail runs near Fitzwilliam for 2025-2026! We've gathered 19 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
8
Saturday

Orange Turkey Trot

5 km
Nov
8
Saturday

Race for DFL

Trail Run 4 mi
Nov
22
Saturday

Roadtown Turkey Trot

5 km
Nov
27
Thursday

Turkey Day 5K - Run Now, Gobble Later

Trail Run 5 km
Nov
27
Thursday

Turkey Trot for Franklin County Community Meals Program

5 km
Nov
27
Thursday

Keene Wobble Gobble 4-Mile Run/Walk

4 mi
Nov
27
Thursday

Brattleboro Turkey Trot

3 mi
January 2026
Jan
1
Thursday

New Year's Day Peanut Butter Chip Chase 5K

5 km
May 2026
May
9
Saturday

Tarc Wapack and Back

Trail Run 22 mi 43 mi 50 mi
May
16
Saturday

Free Spirit 50k

Trail Run 50 km
June 2026
Jun
6
Saturday

Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run

Trail Run 5 mi
Jun
11
Thursday

Hollis Fast

5 km
Jun
27-28
Sa - Su

New England Spartan Event Weekend

Obstacle Run 5 km 10 km
August 2026
Aug
1
Saturday

Savage Race - Boston

Obstacle Run 3 mi 7 mi
Aug
2
Sunday

Greenfield Triathlon

Triathlon
Aug
23
Sunday

New England Green River Marathon

Marathon
September 2026
Sep
27
Sunday

Clarence DeMar Marathon

Half Marathon Marathon
October 2026
Oct
3
Saturday

Friends of the Poor 5K

5 km
Oct
10-11
Sa - Su

Midstate Massive Ultra Trail

Trail Run 50 km 50 mi 100 mi
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