Trail Running calendar near Milford 2026-2027

Take on rugged singletrack and carriage roads at the Frosty Fat Sass, a winter trail running and hiking event in West Orange's South Mountain Reservation. Choose a 5K loop or timed 3 hour and 6 hour options while supporting the South Mounta..

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.

A onesie-themed trail party at Ramapo Valley County Reservation on February 14, 2026, featuring a flat scenic loop around Scarlet Oak Pond. Options include a full 5K (two loops) or a shorter Fun Run of one loop.

Run the Febapple Frozen in South Mountain Reservation, South Orange NJ, where four trail distances loop around a scenic 10 mile course in late February. Expect winter trails, aid stations, swag and timing for a hearty challenge.

Run or hike scenic woodland trails at Mahlon Dickerson Reservation in the Mahlon Winter Donut Run and Hike, with 5 or 10 mile options. All weather welcome and finishers receive a long sleeve shirt, medal and donuts.

Squatchapple is a scenic trail race at South Mountain Reservation in West Orange, NJ, with distances from 11 to 50 miles across three challenging loops. All finishers get a handcrafted wood medal and one shop item.

Enjoy a 34 mile point to point run along the scenic Lenape Trail, riding the train to the eastern start and finishing back at your car. Self supported with varied surfaces and skyline views, the route winds through parks, neighborhoods and..

A paved trail event on March 7, 2026 in Thompson Park, Lincroft featuring a timed 5K and a 1 mile Fun Run; 100% of proceeds benefit Blood Cancer United.

A trail race at Tyler State Park in Newtown on March 7, 2026 offering a 10K and a half marathon, with age group awards, a member discount, and entries transferable if the race is rescheduled.

Take on the MT. TAMMANY 10, a challenging ultramarathon through the scenic Delaware Water Gap on March 21, 2026. Nearly 40 miles and more than 10,000 feet of climbing across ten loops around Mt Tammany promise epic views and a true test of..

Terror of Tammany! on March 22, 2026 in Columbia, NJ is a rugged looped trail challenge with 30K (three 6.7 mile loops) and 50K+ (five loops). Expect technical climbs, a campground start and finish, strict time limits, and finisher awards.

Run the 34 mile Lenape Trail from Branch Brook Park to South Mountain Reservation, passing parks and varied terrain, while supporting clean water projects. Solo runners get full crew support or join a 3 to 6 person relay.

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.

Tackle a rugged, technical 10k through Van Cortlandt Park in the Bronx on March 29, 2026, and grab a commemorative souvenir. A portion of entry fees supports the Van Cortlandt Park Alliance for trail upkeep and youth programs.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

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.

A roughly 5 mile loop around Jacobsburg State Park with 5 mile, 3 hour and 6 hour options on April 4, 2026. The cupless, self supported event includes aid bins for longer efforts and a $1 registration fee for carbon offsets.

Join the 19th Annual Susquehanna Warrior Trail 5K Run and Fun Walk April 4 2026 in Shickshinny, PA along a flat out and back trail. Enjoy Easter themed fun with T shirts, photos with the Easter Bunny, lunch, and trophies for top finishers.

Enjoy a scenic run or walk through maintained natural trails at the Institute Woods 6K in Princeton on April 11, 2026. Choose a 6K or a relaxed 3K, enjoy post run refreshments and a race shirt for early registrants.