Trail Running calendar near Cheshire 2026-2027

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

The NSRF 50/50 Turkey Trot 5K will take place in West Babylon on Sunday 29 November 2026. You can run 5 kilometers.

Repeat a 3.3 mile out and back up the Tower Trail to the Observation Tower at Sleeping Giant. Runners choose a four hour or eight hour format, carry their own hydration, and complete as many laps as they can within the time limit.

A looped ultramarathon in Prospect Park, Brooklyn offering 50 mile and 50 kilometer options. The course uses 3.33 mile loops and includes on course hydration and a potluck style aid station.

A forest trail 5K in Roosevelt Forest, Stratford, CT on December 19, 2026, where participants may run, jog, hike, or walk in costume. Awards go to the three fastest men and women and all finishers receive a commemorative item.

The NSRF 4-Leaf Clover 5K Trail will take place in Old Bethpage on Sunday 28 March 2027. You can run 5 kilometers.

The NSRF The Bunny Trail 5K will take place in Bethpage on Saturday 3 April 2027. You can run 5 kilometers.

A 123-mile point-to-point ultramarathon across Connecticut combining roughly 57 miles of trails with paved backroads, a 36-hour cutoff, relay options, aid stations, on-course medical support, and finish awards including a buckle and event s..

The Big Bear Squatch North will take place in Woodbury on Saturday 3 April 2027. You can run between 10 and 13 miles.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

The Run for the Rescue 5K Trail Run/Walk will take place in Hauppauge on Saturday 10 April 2027. You can run 5 kilometers.

A women only trail race at Lake Mohegan in Fairfield CT offering 5K, 10K and a 4 hour loop option. The event features finisher medals, podium awards, post race food and supports a local non profit.

The Squatchywaska Mountainfest will take place in Ellenville on Saturday 24 April 2027. You can run between 10 and 17 miles.

Squatchywaska Mountainfest in the Shawangunk Ridge on April 24, 2027 features a technical 25K and a 10 mile lollipop course with steep climbs, rocky singletrack, two aid stations, and a six hour cutoff.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.