Trail Running calendar near Massapequa 2025-2026

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, taking place at Harriman State Park in Tuxedo, New York. Participants can choose between a challenging half marathon and a 10K, both featuring rugged terrain, steep climb..

Run The Farm is a running event taking place at Muscoot Farm in Katonah, NY, featuring a 5-mile trail race and two kids' races. Scheduled for October 19, 2025, the event includes a 5-mile race for participants aged 6 and up, along with two kids' races: one for ages 7-12 and another for children aged..

The "8 Hours at the Farm" is a trail running event organized by Steep Endurance, taking place at Gurski Farm/Williams Park in Brookfield, CT. This race features a scenic, approximately 4-mile loop that includes single track and rolling farm trails, fostering a vibrant community atmosphere among part..

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon. Participants will enjoy scenic, rolling courses with views of the Hudson River, featuring fields, stone walls, lakes, and forests. This event supports local organizations, including the ..

The Tarrywile Half Marathon is recognized as one of the most challenging trail half marathons, featuring nearly 3,000 feet of elevation gain and technical Northeast single track terrain. The course offers stunning views of Danbury and serene lakes within Tarrywile Park. Participants can choose from ..

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 aims to ..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, featuring a scenic course that ascends over 600 feet to the Observation Tower. Participants can choose between 4-hour and 8-hour options, completing loops on the Tower Trail, which is approximately 3.3..