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Trail Running Calendar near Old Greenwich 2026-2027

Monthly updates for Old Greenwich

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

Explore the top trail runs near Old Greenwich for 2026-2027! We've gathered 44 exciting races in the area. Check out our detailed list below to find your next local race.

June 2026
Jun
6
Sa

Levee Loop Trail Race 10K - Islip

Trail Run 5 km 10 km
Jun
14
Su

Run in the Park 5K

Trail Run 5 km
Jun
28
Su

Fork in the Trail 5K

Trail Run 5 km
July 2026
Jul
11
Sa

Pinky’s Rock n Rolla

Trail Run 4 mi
Jul
11
Sa

The Revolution

Trail Run
August 2026
Aug
1
Sa

Ridge Reaper Trail Runs

Trail Run 25 km 50 km 50 mi
Aug
8
Sa

Interstate 17 - Closter, NJ

Trail Run 17 mi
September 2026
Sep
19
Sa

Hook Mountain Ultra

Trail Run 27 mi 50 mi
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
Sep
26
Sa

Front Runners New York Cross Country 5K

Trail Run 5 km
October 2026
Oct
11
Su

Paine to Pain Trail Half Marathon

Trail Run Half Marathon
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 ... 26 mi 29 mi
Oct
25
Su

Run The Farm - Katonah

Trail Run 5 mi
November 2026
Nov
7
Sa

Pocantico Hills Marathon

Trail Run 13 mi 26 mi
Nov
8
Su

Raven Rocks Run

Trail Run 10 km 100 km
Nov
8
Su

USATF-Long Island 8K

Trail Run 8 km
Nov
14
Sa

NSRF Long Island Turkey Trail Trot 5K

Trail Run 5 km
Nov
15
Su

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
21
Sa

Storybook Half Marathon

Trail Run 13 mi