Cheshire
Trail Running Calendar near Cheshire 2026-2027
Explore the top trail runs near Cheshire for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
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
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A 10 km rolling loop on technical single track in Penwood State Park, organized by CT Trailmixers, with no aid stations and proceeds partly to 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.
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 races at YMCA Camp Sloper with a 400-minute loop challenge and a 4-mile option on a marked, varied-surface course with aid station support.
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.
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.
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
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.