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Trail Running Calendar near Winchendon 2026-2027

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Explore the top trail runs near Winchendon for 2026-2027! We've gathered 14 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026
Sep
6
Su

Beat the Manure 5K

Road Race Trail Run 3 mi
Sep
13
Su

Pisgah Mountain Trail Races

Trail Run 23 km 50 km
Sep
19
Sa

5K Run for the Rescue

Trail Run 5 km
Sep
19
Sa

Wapack Wilderness Trail Race

Trail Run 18 mi
October 2026
Oct
4
Su

Groton Town Forest Trail Races

Trail Run 3 mi 10 mi
Monthly updates for Winchendon

Get new running races (and updates) in your inbox every month.
Oct
4
Su

Keene Family YMCA Fall Foliage Trail Race

Trail Run 5 km 10 km
Oct
10-11
Sa - Su

Midstate Massive Ultra Trail

Trail Run 30 mi 50 mi 100 mi
Oct
10
Sa

Dublin Trail 5K

Trail Run 3 mi
Oct
17-18
Sa - Su

Ghost Train Trail Races

Trail Run 8 mi 15 mi 30 mi
Oct
25
Su

Granite Gorge Yo-Yo Run

Trail Run 5 mi
Oct
25
Su

Run for the Hills - Harvard

Trail Run 5 km
November 2026
Nov
7
Sa

The Hamsterwheel - New Boston, NH

Trail Run
Nov
7
Sa

Race for DFL

Trail Run 4 mi
May 2027
May
8
Sa

Tarc Wapack and Back

Trail Run 22 mi 43 mi 50 mi
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