Trail Running calendar near Kent 2026-2027

A trail race at South Mountain Reservation on February 21, 2026 offering 50M, 50K, 20M and 10M on an approximately 10 mile loop with aid stations, electronic timing, event SWAG and top-three awards.

A 3 x 2 mile cross country relay at Sunken Meadow State Park in Kings Park, NY, marking the 47th running of the event. The program includes a youth division, a costume contest with prizes, post race refreshments and multiple age categories.

A trail running event at South Mountain Reservation on March 7, 2026 offering five distances across three repeatable loops. The course features mixed surfaces, substantial elevation gain, handcrafted wood medals, and fundraising options for..

Looped hill races at Sunken Meadow State Park where the most distance in a three hour loop crowns the King and Queen, and a separate one hour event crowns the Prince and Princess.

This 5K trail run at Bethpage State Park offers a scenic, mostly flat course through the park's soft trails. Participants receive a themed shirt and can enjoy post-race refreshments, including a free beer for those 21+. The event supports t..

Run or walk a 5K through the scenic Osprey's Dominion Vineyards in Peconic. Registration includes a wine glass, a medal that works as a wine stopper, and a pour of wine. The event is open to all ages and even welcomes leashed dogs.

A low key out and back trail race in Union, Connecticut, following the Nipmuck Trail for about 16 miles of technical, hilly terrain with minimal aid stations and a cap of 100 runners. Proceeds support local trail stewardship.

A trail race at Sleeping Giant State Park in Hamden, CT, built on a 25K loop with a 50K two-loop option. The course features technical singletrack, steep scrambles and an ascent to the Observation Tower.

The Fool's Adventure is a ten hour foot rogaine on March 29, 2026 in Wayne, New Jersey. Competitors navigate more than 100 checkpoints across eight square miles of rugged wilderness using maps and a compass while recording checkpoint eviden..

A rugged, technical trail event in Van Cortlandt Park featuring a two-loop 10k and a Kids Fun Run, with portions of fees supporting local trail maintenance and youth programs.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Trail race at Harriman State Park near Bear Mountain, NY on April 4, 2026. Features a technical 10K with 1,400 ft gain and a half marathon with over 2,600 ft, plus a 10K rucking division and a six hour cutoff.

Timed loop trail races at South Mountain Reservation in South Orange on April 4, 2026. Options include a 1.88 mile loop, a 6K two loop option, and 1 hour, 3 hour and 6 hour timed events.

A 5K run and walk at Bethpage State Park on April 4, 2026 with a free kiddie run and a virtual 5K window, trail terrain, on-site amenities, and proceeds benefiting the Never Stop Running Foundation.

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique *6.55-mile* quarter marathon on the scenic paved trails of West Hartford Reservoir. This small event, limited to 150 participants, features two loops and professional timing. Race day registration is available with a $25 cash f..

A *5K* trail run/walk through Blydenburgh County Park on April 11, 2026 with in-person and virtual options, on-site refreshments and hydration, dog-friendly rules, and proceeds supporting Last Chance Animal Rescue.

A USATF certified point to point half marathon in Albany County on April 11, 2026, mostly on paved rail trail with a net downhill and a 500 foot elevation drop to a Hudson River finish. The event offers live tracking, bus to the start, post..

A community trail event in Cross River, NY on April 12, 2026 featuring a 5k trail race, a 4k walk that skips part of the hill loop, and a 200 meter kids dash on the track.

A spring event at the Stamford Museum and Nature Center on April 12 2026 featuring a scenic 5K through farm and woodland and a 0.3 mile kids run past farm animals. Proceeds support the museum and nature center.