Cheshire
Trail Running Calendar near Cheshire 2026-2027
Explore the top trail runs near Cheshire 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.
November 2026
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.
A trail half marathon at Roosevelt Forest on November 21, 2026 featuring eight 1.64 mile loops, on-course aid, commemorative swag, and podium awards for top male and female finishers.
Trail races at YMCA Camp Sloper featuring a 400 minute multi-loop event and a 4 mile two-lap race, with chip timing, an aid station, and limited fields.
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 at Southington High School features a wooded cross-country course with a track finish, a kids fun run, and awards from Fleet Feet.
3.5 mile trail run and walk around Scoville Reservoir with chip timing, post-race yoga, medals, swag and age-group awards.
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.
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
Eight hour loop event on 1.6 mile laps around Lake Wintergreen in Hamden CT with one aid station, food, a 50 runner limit and proceeds benefiting Doctors Without Borders.
March 2027
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
April 2027
A 6.55 mile race at West Hartford Reservoir on April 10, 2027, run as two 3.275 mile paved loops with chip timing and a 150 runner limit.
50K and 17K loop trail races at Penwood State Park in Bloomfield CT on April 17, 2027 featuring rocky single track, double-track sections, and a cupless aid setup.