Glastonbury
Trail Running Calendar near Glastonbury 2026-2027
Explore the top trail runs near Glastonbury for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A noncompetitive fundraising group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven with a 14-hour cut-off.
A community trail event at Ives Farm featuring a 5K trail race, a team relay for elementary students, a free kids Pumpkin Dash, and family fall activities.
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
Trail races in Burlington CT offering 8K and 5K on mixed technical trails with notable local landmarks and a Burlington Land Trust fundraiser.
October 2026
A 26.4 mile trail marathon in Ashford CT on October 4, 2026 with a two person relay option and a course of rocks, roots, mud, and wood bridges.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
Trail 5K and a kids one mile fun race on a 33 acre campus in Middlefield CT with breakfast treats and finisher medals.
An off road 50K from Guilford Lakes School through rocky forest roads and single track, with aid stations, time cutoffs, and staggered entry fees.
November 2026
A rolling loop trail 10K in Bloomfield CT on November 1 2026 with technical single track, a three hour cutoff, and proceeds partly to NAMI.
A 5K fundraiser at Riverside Park offering run, walk, erg and rowing options to support Riverfront Recapture's community rowing program.
Trail races at YMCA Camp Sloper offering a 400-minute loop event and a 4-mile two-lap race on a roughly two-mile wooded course with one main aid station.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
A Thanksgiving trail event at Scoville Reservoir with a 3.5 mile run or walk, chip timing, post-race yoga, swag, and proceeds supporting the Endometriosis Foundation of America.
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 up and back trail event at Sleeping Giant State Park with four hour and eight hour options and 3.3 mile laps to the Observation Tower.
March 2027
A roughly 16 mile out and back trail race on the Nipmuck Trail in Union CT with minimal aid and proceeds supporting local trail stewardship.
April 2027
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.