Trail Running calendar near Wilton 2026-2027

A trail event at Ward Pound Ridge Reservation combining a 10 kilometer trail race with a November virtual 100k challenge, volunteer support, postrace results, and a finisher woodallion for reported 100k totals.

A community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

The 46th HASHATHON 6-Mile Treacherous Trail Run takes place at Cheesequake State Park on November 8, 2026, featuring a single 6-mile trail race, same-day bib and shirt pickup, post-race beer and pizza, and awards with charity proceeds.

A multi-loop trail event on Staten Island offering a half marathon, 50K, and 50-mile courses that pass through Blood Root Valley, High Rock Park, and La Tourette Park, with proceeds supporting the Greenbelt Conservancy.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half and marathon on technical single track with significant elevation. Finisher medals, awards and a cash bonus for fast half marathoners.

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 *5 miles* lollipop loop trail race in Lewis Morris Park, Morristown NJ, run mostly on the Yellow Trail with roughly 600 feet of elevation gain. The event limits entries to 120 runners, uses cupless stations and hemp bibs, and offers free..

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

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.

A trail party at South Mountain Reservation offering looped 5K terrain and distances from Kids 1M to 50K. The course mixes carriage roads and technical singletrack and features an aid station at the start finish and a charity partner.

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.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Trail races at South Mountain Reservation feature 5K, 10K and 13.1 miles on looped courses over fire roads, single track, hills and pavement, with aid about every three miles and race day registration available.

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 loop-based trail event at Holmdel Park offering 50 km-ish, a Halfish option, and single laps on a varied, mostly off-road course with RFID lap timing and proceeds benefiting MissionCleanWater.

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.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.