Glastonbury
Trail Running Calendar near Glastonbury 2026-2027
Explore the top trail runs near Glastonbury for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races at YMCA Camp Sloper featuring a 400 minute multi-loop event and a 4 mile two-lap race, with chip timing, an aid station, and limited fields.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
Inaugural Stride for the Knights 5K at Southington High School features a wooded cross-country course with a track finish, a kids fun run, and awards from Fleet Feet.
3.5 mile trail run and walk around Scoville Reservoir with chip timing, post-race yoga, medals, swag and age-group awards.
Off-road 5 km and 5 mile run plus a 5 km ruck in South Glastonbury on November 28, with a kids fun run and a post-event chili, s'mores and brewery beverages.
December 2026
Timed trail event at Sleeping Giant State Park with repeated 3.3 mile out and back laps on the Tower Trail and 4 hour or 8 hour options.
A ten-loop, one mile per loop event in Deep River, CT totaling 10 miles, with taco rules, medals per loop, trophies, and proceeds to the Connecticut Forest and Park Association.
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 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
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.
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
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.
A Last Person Standing trail race on Ragged Mountain near Berlin CT with roughly 3.11 mile loops repeated hourly until one runner remains.
June 2027
Point to point trail event along the New England Trail with 112 and 50 mile options; requires crew support, blue blaze navigation, and technical terrain.
A 5K trail and obstacle run on the 400-acre Gaylord Specialty Healthcare campus in Wallingford, CT supporting adaptive sports and hospital fundraising.