Trail Running calendar near Smithtown 2025-2026

The Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run and walk held at Woodtick Recreation, 201 Nichols Road, Wolcott, Connecticut. The event takes place on the scenic and flat Mill Pond Trail, offering a pleasant course for participants. Hosted by the Wolcott Lions Club, the race benefits l..

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 - Katonah is a scenic 5-mile trail race held at Muscoot Farm in Katonah/Somers, New York. Scheduled for October 19, 2025, the event features a main 5-mile race open to participants aged 6 to 108, along with two kids' races: one for ages 7-12 and another for children 6 and under. The rac..

The Bimblers Bluff 50K is an off-road trail race held in southern Connecticut, starting at Guilford Lakes School in Guilford. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky, offering a challenging tes..

The Big Bear Squatchtoberfest is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Organized by Sassquad Trail Running in partnership with the New York-New Jersey Trail Conference, it features a half marathon (13.1 miles) and a 10K race. The courses are technical wit..

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

The Fall Back Into The Trails Series, held at Red Wing Recreation Area in Lagrangeville, NY, offers challenging trail races including a 100K, 50K, and 10K. The 50K consists of five 10K loops with approximately 5,000 feet of elevation gain, while the 100K features ten 10K loops with about 1,000 feet..

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 Rockefeller State Park. The single-loop courses feature rolling hills with scenic views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, streams, forests,..

The Raven Rocks 10k Trail Run is an annual challenging trail race held at Ward Pound Ridge Reservation in Cross River, NY. The course features rugged terrain with rocky climbs, ridgeline trails, hilly meadows, and ravines, ascending to the park's two highest points: Raven Rocks Overlook and the Fire..

The NSRF Long Island Turkey Trail Trot 5K is an annual family-friendly run/walk held at Bethpage State Park in Bethpage, NY. The course starts on a grassy polo field and winds through scenic, mostly flat, beginner-friendly trails with a true cross-country feel. Participants enjoy post-race refreshme..

NYC Trail Mix is an ultra trail running event held in Staten Island, New York, featuring distances of 50 miles, 50K, and a half marathon. The course showcases over 35 miles of trails through the greenest parts of New York City, including Blood Root Valley, High Rock Park, La Tourette Park, and the F..

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. The event fe..

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 trail race where participants complete as many loops as possible on a roughly two-mile course with rolling hills and varied..

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, offering a community-focused a..

The 2025 Never Stop Running Foundation Leftover Turkey Trot 5K is a festive run/walk event held at Bethpage State Park in Bethpage, New York. Participants enjoy a scenic course starting on a grassy polo field and winding through mostly flat, beginner-friendly soft trails with a true cross-country fe..

The Squatchy Leftovers Trail Race takes place at South Mountain Reservation in West Orange, New Jersey. Scheduled for November 29, 2025, it offers multiple distances: 50K, 25K, 10K, 5K, and a 1-mile kids run, all based on a 5K loop course. The trail features a mix of wide carriage roads and technica..

Rob's Trail Run Edition is a trail running event held in Woodbury, New York, at Stillwell Woods Preserve. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those 18 and under. The c..

The Never Stop Running Foundation 50/50 Turkey Trot 5K is a trail run held at Belmont Lake State Park in West Babylon, NY. This fun and challenging 5K event emphasizes community and excitement over competition, offering no traditional awards or swag but a unique raffle where 50% of net proceeds are..

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants can also choose a 5k distance or a virtual race option.Runn..