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.
September 2026
A family friendly obstacle 5k-ish at Stratford Short Beach each September that raises funds for Sterling Community Center programs and services.
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.
Trail races in Burlington CT on September 26, 2026 offering 8K and 5K routes on varied single and double track through Tunxis Trail landmarks.
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 from Guilford Lakes School through rocky forest roads and single track, with aid stations, time cutoffs, and staggered entry fees.
November 2026
Timed trail running on a 4 mile loop at Gurski Farm in Brookfield CT with 8 hour and 4 hour options plus a new 5K Canicross for 2026.
10K trail race in Bloomfield, CT on Nov 1, 2026 featuring technical single-track on the Metacomet Trail 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 race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
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 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.
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.