Trail Running calendar near North Fork 2026-2027

Join the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Run the 4 Leaf Clover 5K at Bethpage State Park on March 8, 2026. Enjoy scenic soft trails, a free kiddie Clover run and a one week virtual 5K, plus a themed shirt while supporting the Never Stop Running Foundation.

Run a chip timed 5k through Osprey's Dominion vineyards on a scenic two lap loop suitable for runners and walkers. Includes a tee, shatterproof wine glass, a finisher medal that doubles as a wine stopper and a pour of wine.

Tackle roughly 16 miles on the scenic, technical Nipmuck Trail in Union, Connecticut, running an out and back through Yale Myers Forest to Boston Hollow. Field capped at 100 with limited aid and no race day registration; proceeds support lo..

Run Sleeping Giant State Park on scenic, challenging trails with 25K and 50K options. Tackle runnable miles, rocky singletrack and a steep scramble to sweeping views, while supporting the park through registration proceeds.

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.

Enjoy the Bunny Trail 5K at Bethpage State Park, starting on a polo field and winding along soft, flat trails. Family friendly with a kiddie run, virtual option, refreshments, and proceeds benefiting the Never Stop Running Foundation.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Join the Run for the Rescue 5K trail run or walk on April 11, 2026 at Blydenburgh County Park in Smithtown, NY, and support Last Chance Animal Rescue. Enjoy scenic trails, dog friendly fun, and optional virtual participation rain or shine.

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

Run a scenic all terrain 5K through Stamford Museum and Nature Center, looping Bendel Pond and passing farm animals. Bring kids for a fun run with Petunia the Scottish Highland cow and support the museum.

Shore2Shore in East Islip on April 18, 2026 offers 50K and 25K trail races along the Long Island Greenbelt Trail, finishing at Heckscher State Park. Enjoy scenic coastline, full aid stations, and a two hour volunteer or donation option.

Take on the Traprock 50 at Penwood State Park in Bloomfield, CT on April 18, 2026. Choose a rugged 50K of three rolling, rocky loops or a single 17K loop along technical single track and scenic forest roads. Bring your own cup.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry at Mercy University for a scenic 7.5k on the Croton Aqueduct Trail. Celebrate Mercy's 75th, snag a commemorative shirt, and support the Mav Market.

Join the Lake Mohegan Women’s Trail Race at Lake Mohegan in Fairfield CT for 5K, 10K or a 4 hour loop challenge open to women and non binary runners. Enjoy scenic trails, finisher medals, post race snacks and a welcoming community vibe.

Celebrate the 52nd Jack Bristol Lake Waramaug Ultra on April 26 in Kent Connecticut with 100K, 50 Miler, and 50K options on scenic rolling loops around the lake. Fast paved roads, four aid stations, and a friendly finish at Lake Waramaug St..

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Take on the VCP50k, a 50 km ultramarathon through Van Cortlandt Park in the Bronx on May 2, 2026, featuring the classic Tortoise and Hare looped course with roots, rocks and 2,200 feet of climbing. Finishers get a custom medal, limited edit..

Blue 2 Blue Challenge is a tough 50K on New Haven's blue blazed trails, featuring rocky technical terrain and big climbs linking West Rock and Quinnipiac. Entry is by vetted waitlist and the race enforces strict cutoffs so come prepared.

Take on scenic singletrack at the Mount Archer Trail Race in Lyme CT on May 3, 2026 with a tough 9.2 mile loop or a fun 3 mile sprint. Chip timed results, post race food and drinks, and proceeds support the Lyme Fire Department and Lyme Amb..