Woodbridge
Trail Running Calendar near Woodbridge 2026-2027
Explore the top trail runs near Woodbridge for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
An eight hour looped run at Lake Wintergreen in Hamden CT with 1.6 mile laps, one aid station, provided food and a 50 runner limit; proceeds benefit Doctors Without Borders.
March 2027
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.
A multi-day August 2027 event at Sacred Heart University with 90 minute stair climb and walk challenges plus a five day virtual step challenge supporting Homes for the Brave.