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Trail Running Calendar near Oyster Bay 2025-2026

Explore the top trail runs near Oyster Bay for 2025-2026! We've gathered 20 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
5
Sunday

IBBC Trail Classic 5k

Trail Run 5 km
Oct
11
Saturday

Gemstone Sparkle Sprint 5k

Trail Run 5 km
Oct
12
Sunday

Paine to Pain Trail Half Marathon

Trail Run Half Marathon
Oct
12
Sunday

NSRF Great Pumpkin Dash Trail 5K

Trail Run 5 km
Oct
19
Sunday

Run The Farm - Katonah

Trail Run 5 mi
November 2025
Nov
2
Sunday

People in Need - Day of the Dead 5k

Trail Run 5 km
Nov
8
Saturday

Pocantico Hills Marathon

Trail Run Half Marathon Marathon
Nov
8
Saturday

Veterans Day Cross Country Run

Trail Run 4 km
Nov
9
Sunday

Raven Rocks 10k

Trail Run 10 km
Nov
15
Saturday

NSRF Long Island Turkey Trail Trot 5K

Trail Run 5 km
Nov
29
Saturday

NSRF Leftover Turkey Trot 5K

Trail Run 5 km
Nov
30
Sunday

NSRF 50/50 Turkey Trot 5K

Trail Run 5 km
December 2025
Dec
7
Sunday

PPTC Endurance Fest

Trail Run 50 km 50 mi
Dec
13-14
Sa - Su

SRC Presents: a Backyard Ultra

Trail Run 4 mi
April 2026
Apr
12
Sunday

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
18
Saturday

Shore2Shore - East Islip, NY

Trail Run 25 km 50 km
Apr
26
Sunday

Leatherman's Loop

Trail Run 10 km
May 2026
May
2
Saturday

VCP 50K

Trail Run 50 km
May
17
Sunday

Spring Run the Farm

Trail Run 5 mi
July 2026
Jul
11
Saturday

Pinky’s Rock n Rolla

Trail Run 4 mi
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