Cheshire
Trail Running Calendar near Cheshire 2026-2027
Explore the top trail runs near Cheshire for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
An obstacle-based 5K at Short Beach in Stratford that raises funds for the Sterling Community Center and includes 18 plus obstacles, shirts, medals and family participation rules.
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
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.
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.
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 in Southington CT with a 400 minute timed loop event and a four mile two lap race organized by CT Trailmixers.
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.