Trail Running calendar near Poughkeepsie 2025-2026

Squatchywaska Mountainfest is an exciting trail running event taking place in Ellenville, NY, featuring two challenging courses: a 25K and a 10-mile race. Participants will navigate stunning mountain singletracks, experiencing breathtaking views of the Catskills and the iconic Verkeerder Kill Falls...

The Wawayanda Trail Fest is an exciting endurance event taking place in Wawayanda State Park, NJ, featuring a variety of race distances including a 100K, 50 Mile, 50K, and Half Marathon. Participants will navigate through scenic trails filled with rhododendron tunnels, marsh bridges, and diverse ter..

The Sterling Squatch Half Marathon, part of the Squatchywaska Mountainfest, offers participants a challenging and scenic experience through the stunning trails of the Shawangunk Ridge. With two course options—10 miles and 25K—runners will navigate rugged terrain, steep climbs, and breathtaking views..

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..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages. The event emphasizes community and outdoor activity, taking place in the scenic Ward Pound Ridge Reservation. Due to its popularity, entry is determined through a lottery system.The r..

The Forgotten Forest Ultra Run, taking place in Stratford, CT, is a unique 9-hour trail running event set in the scenic Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop with an elevation gain of 131 feet per loop. This event is limited to 25 participants, en..

The 47th Annual Woods and Lakes Run is a running event taking place in Mountain Lakes, New Jersey. This event features two races: a traditional 10K and a simultaneous 5K, both open to participants aged 30 and over. The scenic course includes a mix of macadam walkways, gravel paths, and wooded trails..

XTERRA New Jersey is an exciting off-road sports event taking place in Wawayanda State Park, New Jersey. Scheduled for May 3-4, 2025, it is part of the XTERRA World Tour and features a variety of races, including off-road triathlons, duathlons, and trail runs. Participants can choose from multiple d..

The VCP50k is an ultramarathon event taking place in Van Cortlandt Park, Bronx, NY, designed to cater to both novice and experienced runners. Established in 2023, the race features a challenging course consisting of ten loops of a classic cross-country track, with an overall elevation gain of approx..

The MCW Branch Brook Classic is a running event taking place at Branch Brook Park in Newark, NJ, featuring 3-hour and 6-hour races. Set against the backdrop of the Cherry Blossom Festival, participants will navigate a flat 2-mile loop on a soft regenerative rubber surface, ideal for both competitive..

The Frosty Woods - a Winter Way over Yonder Trail Adventure will take place in Ringwood from Saturday 3 May 2025 to Sunday 4 May 2025.

The Bear Mountain Trail Challenge is an exciting running event held at Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K, all set against a backdrop of scenic trails that feature diverse terra..

A Run to Remember is a community-focused running event taking place at The Farm Trails at Greig Farm in Red Hook, NY. Scheduled for May 3, 2025, the event features a 5K Trail Run and a 5K Walk, designed to honor loved ones who have passed away while promoting health and togetherness. Participants ca..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approximat..

The Ansonia Trails 5K is a running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it slightly over or under a traditional 5K distance. Limited to 50 runners, the..

The "3 Days at the Fair" event in Augusta, NJ, is a unique running festival scheduled for May 12-18, 2025. Participants can choose from various timed races, including 144, 72, 48, 24, 12, and 6-hour options, as well as marathon and 50K distances. The course features a certified 1-mile loop on a mix..

The SMR Mayapple Trail Runs, taking place on May 17, 2025, in South Mountain Reservation, NJ, offers a variety of trail races including 50 miles, 50K, 20 miles, 10 miles, 5 miles, and a Kids 1-Mile Run. Organized by the South Mountain Conservancy and supported by volunteers, the event features sceni..

The Tails & Trails State Forest Run, scheduled for May 17, 2025, in Pittsfield, MA, features three race distances: 50K, 25K, and a 5 Miler. This event supports local animal rescue nonprofits, including Red Robin Song Animal Sanctuary, No Paws Left Behind, and Berkshire Bird Paradise, Inc. Participan..

The Run Ragged Last Person Standing event, hosted by the CT Trailmixers, is an exciting endurance race set in the rugged terrain of Ragged Mountain, Berlin, CT. Participants will tackle a challenging 3.11-mile loop, with one hour to complete each lap. The race continues until only one runner remains..