Glastonbury
Trail Running Calendar near Glastonbury 2026-2027
Explore the top trail runs near Glastonbury for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A 10K trail loop in Bloomfield CT on November 1, 2026, on technical single track in Penwood State Park with a three hour cutoff and proceeds supporting NAMI.
A fundraising 5K at Riverside Park supporting Riverfront Recapture's Community Rowing Program with running, rowing, and erg events.
Trail event at YMCA Camp Sloper offering a 400 minute timed loop race and a 4 mile two lap option on a flagged, roughly two mile trail course.
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 on November 22, 2026 at Southington High School features a wooded cross country course and a kids fun run.
Second annual Thanksgiving 3.5 mile trail run and walk around Scoville Reservoir in Wolcott CT supporting endometriosis research with post-race yoga and finisher medals.
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.
Eight hour loop event on 1.6 mile laps around Lake Wintergreen in Hamden CT with one aid station, food, a 50 runner limit and proceeds benefiting Doctors Without Borders.
March 2027
A roughly 16 miles trail race on the Nipmuck Trail near Bigelow Hollow State Park in Union CT with technical terrain, limited aid, and a waitlist.
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.
Trail races at Deer Lake Outdoor Center in Killingworth CT include a timed 5 mile course and a timed 1 mile kids course on technical, well-marked trails.
May 2027
A Last Person Standing trail race on Ragged Mountain in Berlin, CT using repeat one-hour 3.11-mile loops until one runner remains; field limited to 55.
June 2027
Point-to-point trail event on the New England Trail offering 112-mile and 50-mile routes to Guilford, CT, with self-supported crews and route navigation required.