Trail Running calendar near Hauppauge 2025-2026

The Fabulous Fahnestock Trail Races, held in Fahnestock State Park, NY, offer a unique running experience through the scenic Hudson Valley. Participants can choose from three distances: 50K, 25K, and a 5.5-mile race, all featuring a mix of runnable dirt roads and challenging technical single track...

The Barn-B-Q Trail Festival is a unique outdoor celebration held at the restored Masker's Barn in Berkeley Heights, NJ. This event combines trail running and hiking with a lively barn party featuring BBQ, beer, wine, and various activities. Participants can enjoy self-guided trail tours, lawn games,..

The FallApple event in South Orange, NJ, is a diverse running competition scheduled for September 6, 2025. Participants can choose from various distances, including a 5K, 10K, half marathon (13.1 miles), marathon, 50K, and 50 miles. The course will feature a mix of fire roads, single-track trails, h..

The Macedonia Trail Race, held in Macedonia Brook State Park, Kent, CT, offers a unique trail running experience with stunning single track and lush forest trails. Participants can choose from three distances: 50K, 25K, and 12K, each featuring challenging climbs and breathtaking viewpoints. The 25K..

The Pawling 24 Hour Trail Running Festival is an exciting endurance event taking place in Pawling, NY, featuring a variety of race options including 24-hour, 12-hour, 6-hour, and 3-hour challenges. Participants will run on a scenic loop course that combines pavement, grass, and single track trails...

The Storybook Half Marathon is a friendly and inclusive running event taking place in Stratford, CT, on September 13, 2025. Participants can choose to run, jog, hike, or walk the scenic trail course, which features a mix of single and double track trails with some elevation. The event allows up to f..

The Wild Goose Trail Festival, taking place from September 20-21, 2025, at Wawayanda State Park in Hewitt, NJ, offers a variety of trail running events, including distances from 1 mile to 100 miles. This festival features a supportive atmosphere with generous cut-off times, making it ideal for both..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

The Cockaponsett Trails to a Cure is a trail running event taking place in Chester, Connecticut, featuring two race options: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The challenging terrain includes roots, rocks, and hills, with water stations provided along the rou..

The Angevine Farm Trail Festival, hosted by Steep Endurance, takes place in Warren, Connecticut, showcasing the region's scenic trails. This annual event features a variety of races, including an 8-hour challenge, a half marathon, and a 5K, with routes that traverse grassy fields, state forest trail..

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for both individual participants and teams. Scheduled for October 2-5, 2025, it features various challenges, including the Kuwohi, Double K, Denali, Everest, and Olympus Mons Ultra, e..

The Run the Vineyards - Pindar Fall 8K is a scenic running event set in the picturesque Pindar Vineyards in Peconic, NY. Participants can choose between an 8K and a 5K race, both featuring a flat course primarily on hard-packed dirt trails and grass, making it walker-friendly. The event includes chi..

The Tesla Hertz Run is an exciting running event taking place in Rocky Point, NY, featuring various race distances including a 150 Miler, 100 Miler, 100K, 50 Miler, 50K, and 10 Miler. Set in a picturesque area of Long Island, the course offers a scenic 10.48-mile loop through the pine barrens, provi..

The Forbidden Forest 30 Hour Ultra Run is an exciting endurance event set in Stratford, CT, where participants can run, power-hike, or walk for up to 30 hours. This unique race allows entrants to cover distances of 26.2 miles, 50K, 50 miles, 100K, or 100 miles, with the goal of achieving the most mi..

The Paine to Pain Trail Half Marathon is a unique running event set in the scenic woods and trails of five parks in Westchester County, New York. This race features a single-loop course that allows participants to experience diverse terrain, primarily consisting of dirt paths, while enjoying the nat..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..

The Suffolk County Marathon is an annual running event held in Bay Shore, New York, featuring a variety of races including a full marathon, half marathon, 10K, and 5K. Scheduled for October 18-19, 2025, the marathon course starts in the Village of Babylon and finishes in Gardiner Park, West Islip. T..

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 trail running event scheduled for October 19, 2025, at Muscoot Farm in Katonah, NY. The event features a 5-mile race for participants aged 6 and older, alongside two kids' races: one for ages 7-12 and another for children aged 6 and under. The race aims to showcase the beauty of Mu..

The Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School. The course features rolling forest roads and rocky single tracks, providing a challenging experience for runners. Unlike many similar events, participants do not complete the same loop mu..