Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 39 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 8 hour loop event at Lake Wintergreen in Hamden CT with 1.6 mile loops, one aid station, on course snacks and a 50 runner limit. Proceeds support Doctors Without Borders.
March 2027
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
A roughly 16 mile out and back trail race on the Nipmuck Trail in Union, CT with technical terrain, minimal aid stations, and parking at Bigelow Hollow State Park.
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.
A 6.55 mile race at West Hartford Reservoir on April 10, 2027, run as two 3.275 mile paved loops with chip timing and a 150 runner limit.
50K and 17K loop trail races at Penwood State Park in Bloomfield CT on April 17, 2027 featuring rocky single track, double-track sections, and a cupless aid setup.
Women and non-binary runners take on 5K, 10K, or a timed 4 hour loop on the trails around Lake Mohegan in Fairfield, CT.
Timed trail races at Deer Lake Outdoor Center in Killingworth CT include a roughly 5 mile course with about 500 ft of elevation gain and a new timed 1 mile kids run.
May 2027
A 123 miles point to point ultramarathon across Connecticut from East Thompson to Southport, with trail and road sections, a 36 hour cutoff, and relay and 100K options.
Twelve hour trail endurance run on a scenic 5K loop at Chatfield Hollow State Park with individual and relay options and a 100 runner limit.
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.
A rugged Last Person Standing event on Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one runner remains.
June 2027
Multi-day elevation events at Mohawk Mountain offering 12 to 84 hour Solo and team formats, on‑mountain tenting, ski patrol support, and timed lap formats to earn vertical gain.
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.
A 5K trail and obstacle run on the 400-acre Gaylord Specialty Healthcare campus in Wallingford, CT supporting adaptive sports and hospital fundraising.
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.
October 2027
Trail endurance events at Mohawk Mountain Ski Area offering solo and FlexRelay team options across 12, 24, 48, 72 and up to 84 hours with distances from 15 to 152.5 miles.