Trail Running calendar near Milford 2026-2027

Frosty Squatchy on January 31, 2026 in West Orange NJ offers a 5K loop plus three- and six-hour timed trail events and a rucking division. Proceeds support the South Mountain Conservancy and the course mixes carriage roads with rocky single..

Hit the trails at the YETI OR NOT Snowshoe Invasion at Mountain Creek on January 31, 2026. Ride the lift to the top for a scenic 5k or untimed last mile welcoming runners, walkers and first time snowshoers. Bring your own snowshoes.

The Frozen Heart 900 will take place in Rockfall on Saturday 7 February 2026. You can run 50 miles.

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.

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.

Join the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park, a scenic trail run starting on a grassy polo field. Family friendly with a kiddie fun run, virtual 5K and post race refreshments supporting the foundation.

The Ospreys Dominion Wine Run 5K will take place in North Fork on Saturday 21 March 2026. You can run 5 kilometers.

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.

Trail running at Sleeping Giant State Park in Hamden CT with 25K and 50K loop options, steep rock scrambles, aid stations, and a summit at the Observation Tower.

Join the Morris County Empanada Trail on March 29 in Morris Plains NJ with 5K and 10K runs over scenic mixed terrain. Entry includes a long sleeve shirt, finisher medal and an empanada with proceeds benefiting the Arthritis Foundation.

Explore rugged North Jersey wilderness in The Fools Adventure, a 10 hour foot ROGAINE with over 100 checkpoints across scenic, rocky terrain. Test your map and compass skills as you navigate for the best route and enjoy big views.

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.

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.

Join the Spring SOMO Timed Trail Races on April 4, 2026 in South Orange, NJ for looped trail fun at South Mountain Reservation. Pick a one or two loop race or challenge yourself in one, three, or six hour timed events on a 1.88 mile loop.

Run the Bunny Trail 5K at Bethpage State Park for a scenic start on the polo field and winding soft trails with a cross country feel. Family friendly with free kiddie run and virtual option, benefiting the Never Stop Running Foundation.