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Trail Running Calendar near Port Jefferson Station 2026-2027

Monthly updates for Port Jefferson Station

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

Explore the top trail runs near Port Jefferson Station for 2026-2027! We've gathered 25 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
Mar
7
Sa

King of the Hill

Trail Run
Mar
8
Su

NSRF 4-Leaf Clover 5K Trail

Trail Run 5 km
Mar
21
Sa

Ospreys Dominion Wine Run 5K

Trail Run 5 km
Mar
29
Su

Heckscher Classic Trail Race

Trail Run
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
Apr
19
Su

Brookhaven Trail 15K Run

Trail Run 4 mi 15 km
Apr
25
Sa

Lake Mohegan Women's Trail Race

Trail Run 3 mi 6 mi 4 hr
May 2026
May
3
Su

The Blue 2 Blue Challenge

Trail Run 50 km
May
23
Sa

NSRF Long Island Lemonade Trail 5K

Trail Run 5 km
June 2026
Jun
7
Su

Run in the Park 5K

Trail Run 5 km
Jun
13
Sa

Ansonia Six Hour Trail Run

Trail Run
August 2026
Aug
8
Sa

Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk

Trail Run 3 mi
October 2026
Oct
4
Su

Run the Vineyards - Pindar Fall 8K

Trail Run 5 km 8 km
Oct
9-12
Fr - Mo

Tesla Hertz Run

Trail Run 10 mi 50 km ... 100 mi 150 mi
Oct
11
Su

NSRF Great Pumpkin Dash Trail 5K

Trail Run 5 km
Oct
17-27
Sa - Tu

Suffolk County Marathon

Trail Run 5 km 10 km Half Marathon Marathon
November 2026
Nov
8
Su

USATF-Long Island 8K

Trail Run 8 km