Trail Running calendar near North Fork 2025-2026

Tackle scenic single track trails at Grills Preserve in Westerly, RI with a choice of a 10 mile or 10K route through bridges and riverfront. Enjoy post race pizza, refreshments and awards for top finishers and age group standouts.

Run a scenic 5K at historic Ives Farm in Cheshire, CT, with start and finish at the restored barn. Enjoy family friendly fun from a free Pumpkin Dash for kids to music and crafts while supporting the YMCA and Cheshire Land Trust.

Enjoy a scenic off road 5K through beaches, vineyards, ponds and forests at Hallock State Park. Choose in person or virtual and bring kids to a fun run while supporting the Long Island Greenway and enjoying post race wine for ages 21 and up..

Join the 9th annual Fall Back into the Trails at Red Wing Recreation Area in Lagrangeville NY for two days of scenic, supported loop trail racing with 10K 50K and 100K options. Custom finisher medals, camping and UTMB index for longer races..

Event information The People in Need - Day of the Dead 5K is scheduled for Sunday, November 2, 2025, in Fresh Meadows, New York. The event is a charity 5K walk/run organized to raise funds and awareness for People in Need. The event locatio..

Run or stroll through historic Alice Newton Street Park at the Woodbridge Trail Run plus Woodland Walk, with a challenging two loop 4 mile course and an easy 2 mile walk to the falls. Participants receive custom tech T shirts and post event..

Join the Day of the Dead Charity 5K in Fresh Meadows to support People in Need and services for immigrant communities. Enjoy a family friendly two lap course through Cunningham Park with awards for top finishers.

8 Hours at the Farm brings trail runners to Brookfield CT for timed loops on scenic farm and single track trails. Choose 8 hour or 4 hour timed events or a 4 mile race, bring your own cup and race for a handcrafted finisher medal.

Run a chip timed 5k through scenic Stonington Vineyards and celebrate with a wine pour at the finish. Registration includes a soft tee, collapsible wine glass and finisher medal while supporting the Alzheimer's Association.

Choose Marathon or Half Marathon on a single loop through Rockefeller Preserve, a rolling hilly course with Hudson River and Palisades views amid fields, forests and stone walls. Proceeds support local conservation groups.

Join the 45th Annual Veterans Cross Country 4K at the Northport VA Golf Course on Nov 8 to run a scenic grass course and support hospitalized and homeless veterans on Long Island. Post race snacks, awards, and fun runs add family appeal.

Take on the Raven Rocks 10k trail race at Ward Pound Ridge, starting in the meadow and climbing to Raven Rocks Overlook and the Fire Tower Summit. Enjoy rugged woods, a rewarding downhill finish, and support for Friends of Trailside Museum.

Taconic Road Runners FDR Park Cross Country Run is a cross-country race held in Yorktown Heights, New York, at FDR Park. The event features a 6K course that includes almost two miles of the park’s trail system, with most of the route on sof..

Run the Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on Nov 15, 2025. Family friendly with a kiddie dash and proceeds benefiting local youth and athlete development.

Run scenic trails around Watchaug Pond at Burlingame State Park with 8 mile and 4 mile options in the Lil Rhody Runaround. Close out the WTAC Fall Race Series while soaking up classic New England fall scenery.

Run the Brookhaven Trail Half Marathon or 5 Mile through single track, fire trails and sandy woodlands at Brookhaven State Park near Wading River NY. Half marathoners vie for cash, a wood finisher medal and post race refreshments.

Test your trail legs at Tarrywile Park in Danbury CT with technical single track, big climbs, and looped courses for 10K, half, and marathon. Rugged scenery, lively finish, and a standout finisher medal.

Event details Fall Fling 400 is organized by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut on November 22, 2025. The event offers two main entry options: 400-minute run on a roughly two-mile loop 4 Mile (two laps of th..

Brooksvale Trails Turkey Trot : November 23, 2025 The Brooksvale Trails Turkey Trot takes place in Hamden, CT, at Brooksvale Park (524 Brooksvale Avenue). The event is organized by Live Loud Running and the Town of Hamden and is the third a..

Join the Roxbury Thanksgiving Day Charity Race for a festive 5K through Everett B. Hurlburt Community Park. Support local causes and burn off holiday calories with friends and neighbors this Thanksgiving morning.