Trail Running calendar near Upper Nyack 2025-2026

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, 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 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..

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 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 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 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 choose between 5k and 10k distances, both chip-timed, a..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its stunning views and diverse trails. The race features a straightforward course on the Tower Trail, a smooth carriage road that climbs over 600 feet in 1.5 miles to the park's Obser..

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 requirement of some trail experience.Partic..

The Holmdel Classic is a challenging end-of-year trail race held in Holmdel Park, Monmouth County, New Jersey. Featuring a roughly 50K ultra and a half-distance option, the race consists of multiple loops on a 4.65-mile course with 95% trail terrain and 584 feet of elevation gain per lap. The course..

The Frosty Fat Sass is an annual trail running and hiking event held at South Mountain Reservation in West Orange, New Jersey. Participants can choose from a 5K loop, a 3-hour, or a 6-hour endurance challenge, with a new rucking division available for the 3-hour event. The course features a mix of w..

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 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 for those who want to complete..

Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, NY, featuring 25K and 10-mile courses through the scenic Shawangunk Ridge. Runners will navigate rugged, technical singletracks, steep climbs, and breathtaking vistas, including views of the Catskills and Verkeerder..

The Wawayanda Trail Fest, held in Hewitt, New Jersey, is a spring trail running event featuring distances of 100K, 50 miles, 50K, and a half marathon. The course offers a scenic 26+ mile loop through Northern Jersey's hills, including rhododendron tunnels, marsh bridges, gravel roads, and single-tra..