Trail Running calendar near Pleasantville 2026-2027

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 community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY. The route uses sand, dirt roads, hard packed trails and pavement, supports Last Chance Animal Rescue, and is dog friendly with leash rules.

Trail races of 50K and 17K at Penwood State Park in Bloomfield, CT on April 17, 2027. The loop course features rocky single track on the Metacomet Trail and a nine hour cutoff for the 50K.

A two-day Spartan obstacle race weekend at Mountain Creek Resort in Vernon, NJ featuring Sprint, Super, Beast, Ultra and kids races, plus team options, volunteer roles, spectators, and a service member discount.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

Two mountain trail races in the Shawangunk Ridge on April 24, 2027. The technical 25K and 10 mile routes feature cliffs, steep climbs, two aid stations, strong course markings, and a 150 participant cap.

A mountain trail festival near Ellenville NY offering a technical 25K (about 17 miles) and a 10 mile course, both limited to 150 entrants with a six hour cutoff. The routes feature steep climbs, rocky singletrack, and two stocked aid statio..

A two-day multisport event at Stokes State Forest featuring trail runs, off road triathlons, mountain bike races, and paddle triathlon formats with World Series qualification opportunities.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A multi-day timed running festival at the Sussex County Fairgrounds with a certified 1-mile loop, options from 6 to 144 hours plus Marathon and 50K, night lighting, central aid station, camping and electronic lap timing.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

A 5K trail run plus a free kiddie dash at Blydenburgh County Park in Hauppauge, with mixed trail surfaces, on-site parking options, post run refreshments, and proceeds benefiting the Never Stop Running Foundation.

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.

A Spartan obstacle race weekend at Bethel Woods in June 2027 featuring sprint, super and kids races across rolling terrain with obstacles, spectator access, team pricing and a service member discount.

A lake and summit event at Rockland Lake State Park combining a fully accessible 5K paved loop with a rugged 10K trail up Hook Mountain that gains about 1,300 ft and includes steep, rocky sections and one aid station.