Glastonbury
Trail Running Calendar near Glastonbury 2026-2027
Explore the top trail runs near Glastonbury for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Run 56 miles across the entire state of Connecticut on a flat, scenic trail to raise funds and awareness for mental health initiatives.
A community trail event at Ives Farm featuring a 5K, an elementary school relay, a free Pumpkin Dash for young children, family activities, and free training sessions.
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.
Experience a technical trail race through the Nassahegan State Forest and Devil’s Kitchen in Burlington, featuring 5K and 8K distances on the Blue-Blazed hiking trail system.
October 2026
Experience the NipMuck Trail Marathon in Ashford, a 26.4 mile course featuring technical terrain and a relay option through the scenic woods of Connecticut.
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.
A community 5K in Bolton, CT on 10/17/2026 along the Hop River rails to trails, with a $30 entry donated to Project Purple to support pancreatic cancer awareness.
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 through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
November 2026
Run a technical 10k loop through the rocky single track trails of Penwood State Park in Connecticut to support mental health awareness.
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 on November 21, 2026, offering a 400 minute loop challenge and a four mile option with chip timing and an 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.
Inaugural 5K at Southington High School on November 22, 2026 supporting Southington Track & Field, with a campus course and a Kid's Fun Run.
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
Test your endurance at Sleeping Giant State Park by completing as many 3.3 mile loops as possible in 4 or 8 hours on the scenic Tower Trail.