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Trail Running Calendar near Cheshire 2026-2027

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Explore the top trail runs near Cheshire for 2026-2027! We've gathered 24 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

April 2027
Apr
4
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.
Apr
17
Sa

Traprock 50

Trail Run 17 km 50 km
Trail event in Bloomfield CT with 17K and 50K loop courses featuring technical Metacomet Trail single track and rocky forest terrain.
May 2027
May
8
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.
May
15
Sa

Forgotten Forest Ultra Run - Stratford, CT

Backyard Ultra Walk 2 mi
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
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