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Walking Events Calendar near Brattleboro 2026-2027

Explore the top walking events near Brattleboro for 2026-2027! We've gathered 15 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
Oct
10
Sa

Winston Prouty Foliage 5K and Little Leaf Dash

Trail Run
Oct
11
Su

The Village Ultra

Backyard Ultra
Oct
24
Sa

Monster Dash 5K - Northfield

5 km
November 2026
Nov
7
Sa

MDS Run~Walk~Smile

5 km
Nov
7
Sa

Orange Turkey Trot 5K Run/Walk

5 km
Monthly updates for Brattleboro

Get new walking events (and updates) in your inbox every month.
Nov
7
Sa

Harper Grace Memorial 5K Run/Walk

5 km
Nov
11
We

Run 'Round the Mountain Open 10K

5 km
Nov
21
Sa

Roadtown Turkey Trot

5 km
Nov
26
Th

Keene Wobble Gobble 4-Mile Run/Walk

4 mi
Nov
26
Th

Brattleboro Turkey Trot

3 mi
December 2026
Dec
5
Sa

Scores Ugly Sweater Run

5 km
May 2027
May
15
Sa

District Dash 5K - Langdon

5 km
June 2027
Jun-Aug
16-11
We

Scores Summer Series for Scholarships

3 mi
July 2027
Jul
4
Su

4 on the 4th Road Race

4 mi
December 2027
Dec
5
Su

Scores Ugly Sweater Run

3 mi
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