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Trail Running Calendar near Old Saybrook 2026-2027

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Explore the top trail runs near Old Saybrook for 2026-2027! We've gathered 17 exciting races in the area. Check out our detailed list below to find your next local race.

Trail Running Calendar United States
September 2026
Sep
5
Sa

Run for the Hills - Niantic

Trail Run 5 km
Sep
15
Tu

Charlie Stavros Memorial Beach Run

Trail Run 3 mi
Sep
20
Su

Cockaponsett Trails to a Cure

Trail Run 4 mi 9 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
Monthly updates for Old Saybrook

Get new running races (and updates) in your inbox every month.
Oct
17
Sa

Ivoryton Pumpkin Chase

Road Race Trail Run 5 km
Oct
17
Sa

IDS Fearless 5K Run and Walk

Trail Run 5 km
Oct
18
Su

Bimblers Bluff 50k

Trail Run 50 km
Oct
24
Sa

Grills Trail Run

Trail Run 10 km 10 mi
Oct
25
Su

Race for the Greenway 5K

Trail Run 3 mi
November 2026
Nov
8
Su

Stonington Vineyards Wine Run Turkey Trot 5k

Trail Run 5 km
Nov
28
Sa

ODO Gobbler Run & Ruck

Trail Run 5 km 5 mi
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run 3 mi
March 2027
Mar
20
Sa

Ospreys Dominion Wine Run 5K

Trail Run 5 km
April 2027
Apr
4
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
May 2027
May
8
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
June 2027
Jun
5
Sa

Woodland Ramble Trail Run

Trail Run 5 km
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