Trail Running calendar near Wolcott 2026-2027

A trail half marathon in Roosevelt Forest featuring eight laps of a 1.64 mile wooded loop with roots, rocks, and rolling terrain. The event includes a book drive, costume prizes, event swag, and podium awards for top finishers.

A trail event at YMCA Camp Sloper on November 21, 2026, offering a 400 minute timed loop option and a two mile two lap race, with chip timing, a central aid station, and proceeds supporting local organizations.

A community Thanksgiving event featuring a 3.5 mile run and walk around Scoville Reservoir in Wolcott CT, with multiple start waves, post race yoga for participants, finisher medals, volunteers supporting refreshments, and proceeds to EndoF..

A 5K run and walk through Inwood Hill Park in northern Manhattan with a shared start and finish, live results and free finish line photos. Proceeds benefit the Inwood Food Pantry and awards are given to the top two men and women.

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.

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 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 Squatchy Onesie Fest “5K-Marathon” will take place in Mahwah on Sunday 14 February 2027. You can run 5 kilometers.

A 5K trail run and walk at Bethpage State Park with a free kiddie run and virtual option. On-course hydration, post-race refreshments, age-group recognition, and proceeds support the Never Stop Running Foundation.

A spring trail out-and-back on the Nipmuck Trail near Bigelow Hollow, advertised as 16 miles on technical, blazed singletrack with minimal aid and limited parking; proceeds support local trail stewardship.

A community 5K run and free kiddie run on the soft trails of Bethpage State Park, supporting the Never Stop Running Foundation. The event includes in-person and virtual options, refreshments, bib mailing, and age-group recognition.

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..

A mountain trail event at Harriman State Park on April 3, 2027 offering a half marathon, a 10K and a 10K ruck on rugged technical trails with significant elevation gain. Entry is capped at 400 and proceeds support trail maintenance.

Trail races at Sleeping Giant State Park in Hamden, CT offering 25K and 50K loops. The 25K has 3,000 plus feet of vertical gain and varied terrain from carriage roads to steep rock scrambles, with aid stations and postrace food available.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY with mixed trail surfaces, dog friendly rules, on site amenities, live results and proceeds supporting Last Chance Animal Rescue.

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.

Two trail events, 25K (about 17 miles) and 10 miles, on technical singletrack and crushed gravel around the Shawangunk Ridge near Ellenville NY. Routes feature steep climbs, two aid stations, a six hour cutoff and a 150 runner cap.

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.