Guilford
Trail Running Calendar near Guilford 2026-2027
Explore the top trail runs near Guilford for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
March 2027
A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.
Six hour timed trail event at Roosevelt Forest in Stratford CT with a 2.3 mile loop, a 50K option, limited field and awards for top mileage.
April 2027
Trail races at Deer Lake Outdoor Center in Killingworth CT with an approx 5 mile course, about 500 ft of elevation gain, and a timed 1 mile kids run.
May 2027
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.
An elimination loop race on Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one remains; field limited to 55.
August 2027
A scenic 2.5 mile trail run at Wildwood State Park in Wading River benefiting the Friends of Wildwood State Park, with live results and free finish line photos.