Trail Running calendar near Ansonia 2026-2027

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 road ultra in Prospect Park, Brooklyn on Dec 6, 2026 offering 50-mile and 50k options over 3.33-mile loops, with a 15 hour cut-off, Skratch Labs hydration, pot-luck aid, and finisher buckles.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

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.

A winter trail party on a 5K loop offering 5K, 3 hour, 6 hour, and 3 hour rucking divisions, with proceeds benefiting the South Mountain Conservancy. The course mixes carriage roads and technical singletrack with about 300 feet gain per loo..

A onesie-themed 5K at Ramapo Valley County Reservation on February 14, 2027, run on a flat scenic loop around Scarlet Oak Pond. The event is capped at 200 participants, has no cutoff, offers adaptive support, and includes a finisher medal.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

A timed loop event at the Oval in Livingston NJ offering 12 hour, 6 hour, 3 hour and 1 hour races on a USATF certified flat course. Awards include plaques and participants receive a cap or winter hat with an opt out discount.

A multi-loop trail race at South Mountain Reservation offering 11M, 20M, 50K and 50M options on three marked loops with varied terrain, significant elevation gain, a single finish-area aid station, and support for the South Mountain Conserv..

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 point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with trail and road sections, a 36 hour cutoff, relay options, and staffed aid stations.

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.

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..

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 mountain obstacle race weekend at Mountain Creek Resort in Vernon NJ offering Sprint, Super, Beast and Ultra distances plus a Kids Race and spectator access.