Trail Running calendar near Rocky Point 2025-2026

Shore2Shore : Apr 18, 2026 Shore2Shore in East Islip, NY is a point-to-point trail race offering the following distances: 50K 25K The race uses the Suffolk County Long Island Greenbelt Trail. The 50K course runs from Sunken Meadow on the..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high de..

Join the 52nd Jack Bristol Lake Waramaug Ultra Races in Kent CT on April 26, 2026 for 50K, 50 mile or 100K loops around scenic Lake Waramaug. Expect friendly aid stations, post race food and classic New England views.

The VCP50k is an ultramarathon held in Bronx, New York, founded in 2023 and designed to accommodate both novice and experienced runners. The race features a challenging yet accessible course consisting of ten loops on the classic Tortoise a..

Event overview The Blue 2 Blue Challenge is a 50K trail event in New Haven, CT on May 3, 2026. It is held as an out-and-back that starts at West Rock Playground and follows the blue-blazed trail system. Organizers report a slightly over 80%..

Breakneck Point in Beacon, NY on May 3, 2026 is a rugged trail race that challenges seasoned runners with steep, technical terrain and dramatic views. Expect solid aid station support, post race food and memorable swag across 14 or 26 miles..

Forgotten Forest 9-Hour Ultra : May 16, 2026 The Forgotten Forest 9-Hour Ultra takes place at Roosevelt Forest in Stratford, CT (GPS address: 700 Peters Lane). The event is limited to 50 participants. Registration is final; there are no ref..

Event overview Run The Farm is a series of trail races held at Muscoot Farm in Katonah/Somers, NY (51 Route 100, Katonah, NY 10536). The event includes a 5 mile trail race and two age-group kids races (one for ages 7-12 and one for ages 2-6..

Event overview C'mon Armageddon is a trail race held May 17, 2026 in Norvin Green State Park, Old Jungle Habitat, 109 Airport Rd, West Milford, NJ. The event offers multiple race distances and registration opens on Mon. Nov 17, 2025. Awards..

Enjoy the Nipmuck South Trail Race in Mansfield CT, a 15.7 mile out and back along the Fenton River that winds through woods, fields and over small bridges. Organized by Shenipsit Striders, proceeds benefit local trail stewardship.

Event overview The Centurion Ultra Trail Event takes place in Roosevelt Forest, Stratford, Connecticut on Saturday June 27, 2026. The main race challenges runners to complete 100 miles within a 33-hour limit. The field is limited to 50 part..

Pinky’s Rock n Rolla is a unique 4-mile trail race held in Richmond Hill, New York, offering runners an authentic trail running experience on natural hiking trails rather than typical bridle paths or gravel roads. The course, located in For..

Push your limits at the Pawling 24 Hour Trail Festival in Lakeside Park Sept 19 to 20 with timed 3 to 24 hour loop races day or night. Enjoy a scenic loop, food, music and a welcoming runner community.

Wawayanda State Park in Hewitt NJ hosts a trail festival on September 19 and 20, 2026 with races from a kids mile to a 100 mile challenge, evening panels and free camping. Join a welcoming community supporting Bigger Than The Trail.

Run a scenic 13.1 mile trail half in Roosevelt Forest with eight laps on a marked loop, aid on every lap, awards and costume prizes, plus a book drive for local kids. All get a medallion and Athletic Brewing non alcoholic beer.