Trail Running calendar near Pawling 2026-2027

A themed trail event at Ramapo Valley County Reservation with a flat, scenic 1.6 mile lollipop course. Options include a full 5K or a one-loop Fun Run and finishers receive handcrafted medals and aid station support.

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.

Trail event at Mahlon Dickerson Reservation on March 1, 2026 offering 5 mile and 10 mile routes over rugged woodland trails. Participants receive a long sleeved shirt, a medal, and donuts; hikers are welcome.

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..

A self supported, roughly 34 mile run along the Lenape Trail from Newark through parks and reservations to South Mountain Reservation. The route passes Branch Brook Park, Verona Park and Eagle Rock with varied trail surfaces.

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 fully crewed, charity 34 mile run along the Lenape Trail across 18 parks in Essex County. Options include solo or 3 to 6 person relay with regular aid stations, shuttling, first aid and pre event prep resources.

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.

Trail 5K and 10K events in Central Park of Morris County on March 29, 2026, featuring mixed-terrain cross country courses. Entry includes a long-sleeve shirt, finisher medal, and an empanada with a vegetarian option.

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.

Mountain trail event at Harriman State Park on April 4, 2026 offering a half marathon, a 10K and a 10K ruck. Rugged technical courses with substantial elevation gain and a capped field size.

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.

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.