Trail Running calendar near North Fork 2025-2026

Run a scenic 5K at Bethpage State Park with the Never Stop Running Foundation Leftover Turkey Trot, offering in person and virtual options. Free kiddie dash with ribbons and proceeds support the foundation.

Join the Never Stop Running Foundation 50/50 Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30. Half of net proceeds are raffled to participants with winners present and the rest supports the foundation.

Take on the Tower Tag Challenge at Sleeping Giant State Park in Hamden, CT, and run as many 3.3 mile laps as you can in 8 hour or 4 hour formats on a scenic climb to the Observation Tower. Aid station snacks and a finisher medal await while..

Event overview The PPTC Endurance Fest takes place in Prospect Park, Brooklyn, NY on Sunday, December 7, 2025. The event offers two distance options: 50 Miler 50k Registration closes on Thu, December 4 at 11:59 PM ET. Course and event ser..

Event overview The Frosty Forest 5K takes place in Roosevelt Forest in the Town of Stratford, Connecticut on Saturday, December 13, 2025. The event is a trail run over a 5K distance. Participants may wear holiday costumes during the event...

Take on SRC Presents: A Backyard Ultra on Dec 13 to 14, 2025 at Blydenburgh Park, where runners do 4.167 mile laps each hour until one remains. A 1 Lapper runs alongside and proceeds benefit the Long Island Greenbelt Trail Conference.

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Run Seth's Fat Ass 50K on Saturday December 20 2025 at Forest Park in Springfield MA, a friendly looped ultra offering one to ten 5K laps with a seven hour cutoff. Relaxed vibe, easy parking and race day registration welcome runners of all..

Event overview The West Rock Winter Fat Ass Extravaganza is scheduled for December 28, 2025 in Hamden, CT near Lake Wintergreen. The event is an eight-hour looped run using a 1.6-mile loop around Lake Wintergreen with about 65 feet of eleva..

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.

Run scenic, rugged trails at Sleeping Giant State Park with 25K or 50K looped options featuring steep scrambles, runnable singletrack, and a climb to the Observation Tower. Proceeds support the park.

Run the John Jay Community Trail Race in Cross River on Sunday April 12, 2026 for a scenic 5k through wooded, hilly school trails and a family friendly 4k walk. Kids can sprint the 200 m Jay Dash on the track and celebrate a student built c..

Join the Connecticut Traprock trail ultramarathon for community spirit and scenic challenge with 17 km and 50 km options. Held the Saturday before the Boston Marathon at Penwood State Park, this festive race draws trail runners of all level..

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..

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.

Leatherman's Loop is a scenic spring trail 10k in Cross River, NY, welcoming runners of all levels to enjoy winding park trails on April 26, 2026. Entry is by lottery and the fee includes park admission.

Challenge yourself at VCP50k, a scenic but rugged 50k ultramarathon in the Bronx on May 2, 2026. Ten loops of classic cross country trail bring rocks, roots and rolling climbs with stocked aid stations, a custom finisher singlet and post ra..

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%..