Trail Running calendar near Poughkeepsie 2025-2026

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, takes place in Rockefeller State Park and features a scenic, rolling, and hilly course with views of the Hudson River and Palisades. Participants can choose between the full marathon and half marathon, both of which pass through picturesque la..

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 scenic views including the site of the former fire tower. The event fosters a vibra..

NYC Trail Mix is an exciting ultra trail running event taking place in Staten Island, New York, on November 15, 2025. This event features three race distances: a 50-mile, a 50K, and a half marathon, all set against the backdrop of over 35 miles of scenic trails. Participants will explore unique loca..

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. Runners can..

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 with varied terrain, including wo..

The Squatchy Leftovers Trail Race, taking place on November 29, 2025, at South Mountain Reservation in West Orange, NJ, offers a variety of distances including 5K, 10K, 25K, and 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost-free thera..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event not only..

The Santa's Summit 10k is a scenic and challenging trail race held along the Bull Run Occoquan Trail at Bull Run Marina. Participants can choose between the 5k and 10k distances, with the event featuring chip timing, finisher medals, and technical event shirts. The course is hilly and partly out-and..

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 exciting running event taking place in Prospect Park, Brooklyn, featuring both a 50-mile and a 50-kilometer race. Participants will navigate a looped course that honors NYC's ultramarathon heritage, completing either 9 or 15 loops of 3.33 miles each. The event encourage..

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 requirement of some trail experience.Partic..

The Mahlon Winter Donut Trail Run & Hike features a scenic adventure through the beautiful trails of Lake Hopatcong, NJ. Scheduled for February 8, 2026, participants can choose from three distances: a 5-mile, 10-mile, or half marathon (13.1 miles). The courses offer a mix of terrain, including strea..

The Livingston Oval Ultra is a 2026 ultramarathon event held in Livingston, NJ, featuring races of 1, 3, 6, and 12 hours. Participants run around a USATF-certified, fast, and flat oval course, aiming to cover as much distance as possible within their chosen time frame. The event offers a supportive..

Squatchapple is a trail running event held at South Mountain Reservation in West Orange, NJ, offering distances of 11 miles, 20 miles, 50K, and 50 miles. The race features three distinct loops—4, 5.5, and 7 miles—with varied terrain including carriage roads, singletrack, and some road crossings, all..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event featuring 25K and 50K distances. Known as one of the toughest races in the Northeast, the course offers over 3,000 feet of vertical gain per 25K loop, with a mix of smooth ca..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Connecticut, marking its 51st anniversary. This historic race features three distances: 100K, 50 miles, and 50K, all set around the scenic Lake Waramaug. Participants can expect well-st..