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Walking Events Calendar near Shelter Island 2026-2027

Explore the top walking events near Shelter Island for 2026-2027! We've gathered 48 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
Oct
31
Sa

St. Michael School Turkey Trot 5K

Oct
31
Sa

CFA 5K Run & Walk for Mental Health

2 mi 5 km
Oct
31
Sa

Southold Athletic Association 5K & Fun Run

5 km
November 2026
Nov
7
Sa

Tarzan Brown Mystic River Run

Nov
8
Su

Stonington Vineyards Wine Run Turkey Trot 5K

Trail Run 5 km
Monthly updates for Shelter Island

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Nov
8
Su

The Dock Closing 3.3 Mile Race

3 mi
Nov
11
We

Veterans Day 5K Run/Walk - Wading River

5 km
Nov
14-15
Sa - Su

The Witching Hours

Trail Run
Nov
14
Sa

Hudsy 5K Run/Walk

5 km
Nov
21
Sa

Waterford High School 5K Turkey Trot

5 km
Nov
26
Th

Branford Thanksgiving 5K

2 mi
Nov
26
Th

Turkey Trot - Madison, Connecticut

2 mi
Nov
26
Th

Montauk Turkey Trot Run for Fun

3 mi 6 mi
Nov
26
Th

EMO Turkey Trot 5K - East Moriches

5 km
December 2026
Dec
6
Su

Stuff the Sleigh 5K Run/Walk

5 km
Dec
12
Sa

Niantic Jingle Bell 5K

5 km
Dec
12
Sa

Every Day's A Beach Day 5K

5 km
January 2027
Jan
1
Fr

Frosty 5K - Guilford

2 mi
March 2027
Mar
20
Sa

Ospreys Dominion Wine Run 5K

Trail Run
April 2027
Apr
17
Sa

Katy's Courage 5K Run/Walk

5 km
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