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Trail Running Calendar near Sag Harbor 2025-2026

Explore the top trail runs near Sag Harbor for 2025-2026! We've gathered 37 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
19
Sunday

Bimblers Bluff 50k

Trail Run 50 km
Oct
19
Sunday

Run for the Cove & Memorial Walk

2 mi 5 km
Oct
19
Sunday

Addy’s Run

5 km
Oct
26
Sunday

Race for the Greenway 5K

Trail Run 5 km
November 2025
Nov
1
Saturday

Southold Athletic Association 5K & Fun Run

5 km
Nov
8
Saturday

Hudsy 5K Run/Walk

5 km
Nov
8
Saturday

EBAC Fall Challenge

5 mi
Nov
16
Sunday

Brookhaven Trail Half Marathon

Trail Run 5 mi 21 km
Nov
27
Thursday

EMO Turkey Trot 5K

5 km
Nov
27
Thursday

Montauk Turkey Run For Fun 3 & 6 Mile Run/Walk

3 mi 6 mi
December 2025
Dec
13
Saturday

Niantic Jingle 5K

5 km
Dec
14
Sunday

Jingle Bell Run - Madison

5 km
May 2026
May
2
Saturday

Brew Run - New London

5 km
May
23
Saturday

Run for Briggs 5K

5 km
July 2026
Jul
12
Sunday

Jamesport Triathlon

Triathlon
Jul
18
Saturday

Joe Koziarz 5K Run/Walk

5 km
August 2026
Aug
2
Sunday

Race of Hope Southampton

5 km
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