Trail Running calendar near Ansonia 2025-2026

Fall Back Into The Trails Series returns to Red Wing Recreation Area in Lagrangeville, NY for its 9th annual edition on November 1-2, 2025. The event offers three races: 100k (10x10k loops with about 1,000 ft of gain per lap), 50k (5x10k loops with about 5,000 ft total gain), and 10k (about 1,000 ft..

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 location is listed as 7311 Utopia Parkway, Fresh Meadows, NY 11366. The organizing g..

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..

Stonington Vineyards hosts the Wine Run Turkey Trot 5k at Stonington Vineyards in Stonington, CT. This timed 5k offers a run or walk on a two-lap cross-country course that begins and ends at the winery, weaving through vineyard lanes with occasional uneven footing. The atmosphere blends fitness with..

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..

The Veterans Day Cross Country 4K Run, hosted by the Northport Running Club, is held at the Veterans Administration Medical Center Golf Course in Northport, NY. The English-style 4K course runs entirely on grass (about 2.48 miles) with no pets or baby joggers allowed. In its 45th year, the event ben..

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 soft surfaces across flat fields and picnic areas near the Taco..

The Centerville Bank Thompson Turkey Trot is an annual event held at the West Thompson Dam Overlook Shelter in Thompson, Connecticut. It features a 5K timed trail run, a 3K untimed walk called the "Wobble" where dogs on leashes are welcome, and a free kids' fun run for children 12 and under. The eve..

The Raven Rocks Run is a trail event held at Ward Pound Ridge Reservation in Cross River, NY. The in-person event includes a 10k trail run that climbs to the park's high points, passing Raven Rocks Overlook and the Fire Tower Summit and the site of the former Cross River Mountain Fire Tower. The co..

NSRF Long Island Turkey Trail Trot 5K is a family-friendly trail run/walk held at Bethpage State Park, Polo Field in Bethpage, NY. The 5K course takes participants through scenic, grassy polo-field starts into winding soft trails with mostly flat terrain and a few small hills, offering a beginner-fr..

NJ Trail Series SOMO Winter 1 is a trail running event held in South Orange, New Jersey, at South Mountain Reservation, with distances of 5K, 10K, and 13.1 miles on a looped course. The route blends fire roads, single-track, hills, and some pavement, offering a mix of terrain. Runners complete 1 loo..

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..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers three distances—10K, Half Marathon, and Marathon—through rugged park trails. The course is renowned for substantial elevation and technical Northeast single-track sections, delivering views of Danbury and the park’s tran..

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..

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..

NSRF Leftover Turkey Trot 5K at Bethpage State Park (Polo at the Park) offers a 5K Run/Walk on grassy polo-field and scenic trails, with mostly flat, beginner-friendly terrain and some rolling sections reminiscent of cross-country. The event, held Nov 29, 2025, features a free Kiddie Dash before the..

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..

NSRF 50/50 Turkey Trot 5K is an in-person trail run/walk held at Belmont Lake State Park in West Babylon, New York. The event features a 5K trail course around the park’s water-side setting, described as a fun and challenging route. Participants compete not for traditional awards but for a cash raff..