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Running Calendar near Brattleboro 2026-2027

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Explore the top running races near Brattleboro for 2026-2027! We've gathered 27 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
October 2026
Oct
3
Sa

The Great River Challenge

Cross Triathlon Short Course 4 2.5 3.75 mi Solo Triathlon SUP Short... 4 2.5 3.75 mi 2 Person Relay Team Triat... 4 2.5 3.75 mi 3 Person Relay Team Triat... 4 2.5 3.75 mi
Oct
4
Su

Covered Bridge Classic

10 km
Oct
4
Su

Keene Family YMCA Fall Foliage Trail Race

Trail Run 5 km 10 km
Oct
10
Sa

Dublin Trail 5K

Trail Run 3 mi
Oct
10
Sa

Winston Prouty Foliage 5K and Little Leaf Dash

Trail Run 5 km
Monthly updates for Brattleboro

Get new running races (and updates) in your inbox every month.
Oct
11
Su

The Village Ultra

Backyard Ultra
Oct
11
Su

CLTA 5K in Memoriam of Major General KO Sanborn

Trail Run 5 km
Oct
17
Sa

Mahar Cancer Fund Run/Walk 5K

5 km
Oct
24
Sa

Monster Dash 5K - Northfield

5 km
Oct
25
Su

Granite Gorge Yo-Yo Run

Trail Run 5 mi
Oct
25
Su

Spofford Lake 10K

10 km
November 2026
Nov
6-8
Fr - Su

Race for DFL

Trail Run 4 mi
Nov
7
Sa

MDS Run~Walk~Smile

5 km 10 km
Nov
7
Sa

Orange Turkey Trot 5K Run/Walk

5 km
Nov
7
Sa

Harper Grace Memorial 5K Run/Walk

5 km
Nov
11
We

Run 'Round the Mountain Open 10K

5 km 10 km
Nov
21
Sa

Roadtown Turkey Trot

5 km
Nov
26
Th

Gobble Gobble Wobble 5K

5 km
Nov
26
Th

Keene Wobble Gobble 4-Mile Run/Walk

4 mi
Nov
26
Th

Brattleboro Turkey Trot

3 mi
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