Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 52 exciting trail runs across the region. Find your next trail run in Connecticut below and join the trail community at these great events!
December 2026
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
A six-hour trail ultra at Roosevelt Forest featuring a 2.3-mile loop with 191 feet of climb per lap, chip-timed laps, on-course aid and food, podium awards, medallions for over four hours, and a limited field supporting local charities.
A roughly 16 mile trail race on the Nipmuck Trail in Union CT with minimal aid stations, limited parking at Bigelow Hollow State Park, and a waitlist instead of race day registration.
April 2027
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.
Point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with solo and relay options, 36 hour cutoff and mixed trail and road course.
Trail loop races at Penwood State Park in Bloomfield CT offering 17K and 50K on rocky single-track and double-track, organized by the CT Trailmixers.
Women and non-binary runners take on 5K, 10K, or a timed 4 hour loop on the trails around Lake Mohegan in Fairfield, CT.
May 2027
Family Color Run plus a 5K trail run and 5K trail walk at Camp Mountain Laurel in Hamden on May 15, 2027, with pre-registration benefits and on-site registration.
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.
June 2027
Timed 5K trail run at Coogan Farm in Mystic CT through meadows, woods and fields, capped at 150 runners with tiered fees and youth pricing.
August 2027
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.