Trail Running calendar near North Fork 2025-2026

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

Run The Farm in Katonah, NY, is a scenic 5-mile trail race held at Muscoot Farm, designed to showcase the park's natural beauty and promote local farmers' markets. Scheduled for October 19, 2025, the event features a main 5-mile race open to ages 6 to 108, along with two kids' races: one for ages 7-..

The Bimblers Bluff 50K is an off-road trail race held in southern Connecticut, starting at Guilford Lakes School. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky. Unlike many ultras, the route does not..

The Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Grills Preserve in Westerly, Rhode Island. Participants can choose between a 10-mile and a 10K race, both showcasing the scenic trails and natural beauty of the area, in..

The Fall Back Into The Trails Series is an annual trail running event held at Red Wing Recreation Area in Lagrangeville, NY. The 2025 edition features three race distances: a challenging 100K (10 loops of 10K each with about 1000ft elevation gain per lap), a 50K (5 loops of 10K with approximately 50..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop combining single track and farm trails, offering a scenic and community-focused atmosphere. Participants can choose..

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, offers both marathon and half marathon distances through the scenic Rockefeller State Park. The single-loop courses feature rolling hills with picturesque views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, st..

The Raven Rocks 10k Run is an annual trail race held at Ward Pound Ridge Reservation in Cross River, NY. Known for its challenging course, the race features rocky climbs, ridgeline trails, hilly meadows, ravines, and the historic fire tower site, offering scenic views of Long Island Sound, Connectic..

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, the event features two race options: an 8-mile course and a 4-mile course, both set against the scenic backdrop of Watchaug Pond. This ra..

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is known as one of the toughest trail half marathons in the region. The challenging course features nearly 3,000 feet of elevation gain and technical Northeast single-track terrain. Runners enjoy stunning views of Danbury a..

The Fall Fling 400 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. It features two main races: a 400-minute timed event where participants run as many loops as possible on a roughly two-mile trail course, and a 4-mile race consisting of..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course through the scenic park setting..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its scenic views and historic Observation Tower. Participants run repeated loops on the Tower Trail, a smooth carriage road ascending over 600 feet in 1.5 miles to the tower, then ret..

The PPTC Endurance Fest is an ultramarathon event held in Brooklyn, NY, featuring 50-mile and 50-kilometer race options. The race takes place on a looped course within Prospect Park, consisting of 9 or 15 laps of a 3.33-mile loop. Starting and finishing near the Lincoln Road Entrance, the event hono..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K race offers participants a chance to escape the road and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are welcome, with a recommendation for some trail experience.Pa..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop with over 3,000 feet of vertical gain and a 50K option consisting of two loops. The c..

Leatherman's Loop is a renowned 10k trail race held annually each spring at the Ward Pound Ridge Reservation in Cross River, New York. Established in 1987, it is considered the largest trail race on the East Coast of the United States. The event features a challenging and scenic course through the r..

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event featuring 100K, 50-mile, and 50K distances. The course consists of rolling loops primarily on flat, paved roads around scenic Lake Waramaug, known for personal record performances. Runners enjoy..