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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 19 exciting races in the area. Check out our detailed list below to find your next local race.

April 2026
Apr
26
Su

Deer Lake Trail Run

Trail Run 5 mi
May 2026
May
2
Sa

Chocolate Truffle Shuffle 5K Trail Run

Trail Run 5 km
May
3
Su

Mount Archer Trail Race

Trail Run 3 mi 9 mi
May
9
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
May
17
Su

Double Helix Race

Trail Run 2 mi
May
30
Sa

Woodland Ramble Trail Run

Trail Run 5 km
June 2026
Jun
20
Sa

Summer Solstice Trail Run

Trail Run 3 mi 5 mi 8 mi
Jun
27
Sa

Brooksvale 12-Hour

Trail Run
July 2026
Jul
10
Fr

Rails-to-Trails 5K - East Hampton

Trail Run 5 km
August 2026
Aug
5
We

Stonington Cross Country 5K

Trail Run 5 km
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
Oct
18
Su

Bimblers Bluff 50k

Trail Run 50 km
Oct
24
Sa

Grills Trail Run

Trail Run 10 km 10 mi
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run
April 2027
Apr
4
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
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