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Walking Events Calendar near Great Barrington 2026-2027

Explore the top walking events near Great Barrington for 2026-2027! We've gathered 16 great walks in the area. Check out our detailed list below to find your next local walk.

September 2026
Sep
5
Sa

Run the Dam for Davenport

Road Race Trail Run 2 mi
Sep
19
Sa

Hope House 5K Trail Run and Walk for Recovery

Trail Run
Sep
19
Sa

Camphill Village 5K Trail & Fun Run

Trail Run 5 km
October 2026
Oct
1-4
Th - Su

IronHike Endurance Series

Trail Run Backyard Ultra
Oct
4
Su

Germantown Library 5K

Monthly updates for Great Barrington

Get new walking events (and updates) in your inbox every month.
Oct
4
Su

GBLC Walk for Conservation

2 mi 5 mi
Oct
10
Sa

Chesterwood 5K Walk & Run

5 km
Oct
11
Su

Mohawk Mountain Race

Trail Run
Oct
11
Su

Lime Rock Park 5K

Oct
17
Sa

The Little Guild Run & Wag 5K

Oct
18
Su

Run for the Revolution

Oct
18
Su

SMP Lymphoma Research Foundation Charity 5K

Trail Run 5 km
Oct
24
Sa

Monster Dash 5K - Great Barrington

Oct
25
Su

Ghostly Gallop - Hudson

5 km
November 2026
Nov
21
Sa

Berkshire Mini-March for the Food Bank

3 mi
Nov
26
Th

Thankful 5K - Pittsfield

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