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Trail Running Calendar near Massapequa 2025-2026

Monthly updates for Massapequa

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

Explore the top trail runs near Massapequa for 2025-2026! We've gathered 14 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
Mar
8
Su

NSRF 4-Leaf Clover 5K Trail

Trail Run 5 km
April 2026
Apr
4
Sa

NSRF The Bunny Trail 5K

Trail Run 5 km
Apr
11
Sa

Run for the Rescue 5K Trail Run/Walk

Trail Run 5 km
Apr
12
Su

Farm & Forest All-Terrain 5K

Trail Run 5 km
Apr
18
Sa

Shore2Shore - East Islip, NY

Trail Run 25 km 50 km
May 2026
May
2
Sa

VCP 50K

Trail Run 50 km
May
23
Sa

NSRF Long Island Lemonade Trail 5K

Trail Run 5 km
July 2026
Jul
11
Sa

Pinky’s Rock n Rolla

Trail Run 4 mi
October 2026
Oct
11
Su

Paine to Pain Trail Half Marathon

Trail Run Half Marathon
Oct
17-27
Sa - Tu

Suffolk County Marathon

Trail Run 5 km 10 km 13 mi 26 mi
November 2026
Nov
14
Sa

NSRF Long Island Turkey Trail Trot 5K

Trail Run 5 km
Nov
26
Th

Inwood Hill Turkey Trot

Trail Run 5 km
Nov
28
Sa

NSRF Leftover Turkey Trot 5K

Trail Run 5 km
Nov
29
Su

NSRF 50/50 Turkey Trot 5K

Trail Run 5 km