Cheshire
Trail Running Calendar near Cheshire 2026-2027
Explore the top trail runs near Cheshire for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
November 2026
Timed trail running at Gurski Farm in Brookfield CT on a rolling four mile loop with 8 hour, 4 hour, and a new 5K canicross option.
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.
A 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
Trail event at Alice Newton Street Park in Woodbridge CT offering a 4 mile trail run and a 2 mile woodland walk, with shirts, refreshments and awards.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
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.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
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.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
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.