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Trail Running Calendar near Old Saybrook 2026-2027

Monthly updates for Old Saybrook

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

Explore the top trail runs near Old Saybrook for 2026-2027! We've gathered 11 exciting races in the area. Check out our detailed list below to find your next local race.

February 2026
Feb
7
Sa

Frozen Heart 900

Trail Run 50 mi
March 2026
Mar
21
Sa

Ospreys Dominion Wine Run 5K

Trail Run 5 km
Mar
29
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
May 2026
May
3
Su

Mount Archer Trail Race

Trail Run 3 mi 9 mi
August 2026
Aug
5
We

Stonington Cross Country 5K

Trail Run 5 km
September 2026
Sep
12
Sa

Run for the Hills - Niantic

Trail Run 5 km
Sep
15
Tu

Charlie Stavros Memorial Beach Run

Trail Run 3 mi
October 2026
Oct
3
Sa

Run for the Pumpkins Trail Run

Trail Run 5 km 10 km
Oct
4
Su

Run the Vineyards - Pindar Fall 8K

Trail Run 5 km 8 km
Oct
24
Sa

Grills Trail Run

Trail Run 10 km 10 mi
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run