Trail Running calendar near Wading River 2025-2026

The Fall Back Into The Trails Series will take place in Lagrangeville on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

Stonington Vineyards Wine Run Turkey Trot 5k is a timed 5k run/walk held at Stonington Vineyards in Stonington, Connecticut. The two-lap cross-country course begins and ends at the winery, winding through vineyard lanes with some uneven footing, suitable for runners and walkers alike. The Thanksgivi..

8 Hours at the Farm is a trail running event by Steep Endurance in Brookfield, Connecticut, on the rolling grounds of Gurski Farm/Williams Park. The race features approximately a 4-mile loop weaving single-track and farm trails, delivering a rolling, not-too-technical course and a supportive trail-r..

Set in Sleepy Hollow, New York, the Pocantico Hills Marathon offers two distances: a full marathon and a half marathon run through Rockefeller State Park Preserve. The courses are single loop, rolling and hilly, with scenic views of the Hudson River and the Palisades. Runners pass past fields, stone..

Raven Rocks Run is a challenging 10k trail race held at Ward Pound Ridge Reservation in Cross River, New York. The route climbs to the park’s highest points, including Raven Rocks Overlook and the Fire Tower Summit, before a mostly downhill finish along rugged ridgelines, rocky climbs, meadows, and..

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 annual 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, an..

Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It is the fourth and final race in WTAC’s Fall Trail Race Series, offering two trail distances: 8 miles and 4 miles on Watchaug Pond area trails. Expect a classic, wooded trail course around the pond, with..

Located in Brookhaven State Park, Wading River, NY, the Brookhaven Trail Half Marathon and 5 Mile offer two trail-running distances. The course traverses a mix of Suffolk County woodlands, including single-track, fire roads, sandy sections, and hidden ponds, starting near the park entrance off Willi..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers Marathon, Half Marathon, and 10K trail distances. The course is renowned for its toughness, with close to 3,000 feet of elevation and substantial Northeast single-track, featuring rocky, rooty, and hilly terrain. The rou..

Fall Fling 400, the CT Trailmixers’ ninth annual trail race, takes place at YMCA Camp Sloper in Southington, CT. The event offers two options: Fall Fling 400, where runners complete as many roughly two-mile loops as possible within a 400-minute limit (roughly 28 miles minimum), and the Spring Fling..

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..

Tower Tag Challenge is held at Sleeping Giant State Park in Hamden, Connecticut. The course follows the Tower Trail, a crushed-gravel carriage road that climbs about 600 feet in 1.5 miles to the Observation Tower, offering sweeping park views and, on clear days, Long Island Sound. Each Tower Tag att..

PPTC Endurance Fest in Brooklyn’s Prospect Park offers 50-mile and 50-kilometer ultramarathon options on a looped course of 9 or 15 laps of 3.33 miles. The race begins and ends near the Lincoln Road Entrance and honors NYC’s road-ultra heritage, including Knickerbocker 60k and Metropolitan 50 Mile...

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail exp..