Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 49 exciting trail runs across the region. Find your next trail run in Connecticut below and join the trail community at these great events!
March 2027
A limited-field 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 50K option on a 2.3 mile loop through roots, rocks and rolling hills.
A roughly 16 mile out and back on the Nipmuck Trail in Union CT with minimal aid stations, blue blazes, and proceeds supporting local trail stewardship.
April 2027
A point to point 123 mile ultramarathon across Connecticut on April 3, 2027, featuring trail and road sections, aid stations, five intermediate cutoffs and a 36 hour limit.
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.
Trail event in Bloomfield CT with 17K and 50K loop courses featuring technical Metacomet Trail single track and rocky forest terrain.
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
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.
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.
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.