Trail Running calendar near Smithtown 2025-2026

The Where the Pavement Ends Single & Double Loop is a trail running event held in Ridgefield, Connecticut, starting and finishing at the Lake Windwing ballfields. Scheduled for September 14, 2025, the race offers two options: a 4.25-mile single loop and an approximate 8-mile double loop through the..

The Charlie Stavros Memorial Beach Run is a free, 3-mile race held at Westerly Town Beach in Westerly, Rhode Island. Organized by the Westerly Track Club and the Stavros family, this event takes place at low tide, featuring a scenic out-and-back course of 1.5 miles each way along the beach. The run..

The Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey, offering a variety of trail running events over September 20-21, 2025. Distances range from a 1-mile kids run to a challenging 100-mile ultramarathon with a generous 36-hour cutoff, making it ideal for first-tim..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience through grassy fields, land trust trails, state forest paths, single track, and dirt roads. The event features multiple distances including a half marathon, a new 8-hour r..

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..

The Cockaponsett Trails to a Cure is a trail running event held in Chester, Connecticut, within the Cockaponsett State Forest. Participants can choose between a 4-mile or a 9-mile race, with the shorter distance covering the first part of the longer course. The trail features natural terrain includi..

The Front Runners New York Cross Country 5K is an annual running event held at Van Cortlandt Park in the Bronx, New York. Celebrating its 22nd year in 2025, the race offers a scenic 5K cross-country course through the park's fall landscape. Participants meet at the iconic Tortoise & Hare Sculpture f..

The IronHike Endurance Series at Mohawk Mountain Ski Area in Cornwall, CT, is a multi-day endurance event held over four days in October 2025. Participants can choose from various challenges ranging from 12 to 84 hours, covering distances from 15 miles to over 150 miles with significant elevation ga..

The Run for the Pumpkins Trail Run, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

The CFA Trail 5K & Children's Fun Run for Mental Health is a timed trail running event held at Deans Mill Farm in Stonington, Connecticut. Participants can choose between a 5K trail run or a fun run for children aged six and under. The race takes place amid beautiful fall foliage, offering a scenic..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K and an 8K race, both on mostly flat, hard-packed dirt trails and short-cut grass, making the e..

The Fat Sass Switchback Challenge is a trail running event held in Millburn, New Jersey, at the South Mountain Reservation's Locust Grove Picnic Area. Scheduled for October 5, 2025, it offers three race options: a 5K, a 3-hour, and a 6-hour challenge. Participants run a 1-mile loop featuring a steep..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, featuring 3-hour and 6-hour race options. Participants run on a challenging 2.33-mile loop course in Kakiat Park, adjacent to Harriman State Park, with approximately 660 feet of vertical gain per lap. The course offer..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The 12th edition features three trail race distances: a challenging 5K through Barbour Woods with scenic climbs and wetlands; a 10K that adds a tough loop summiting Haystack..

The Tesla Hertz Run is an ultramarathon event held in Rocky Point, New York, featuring multiple race distances including 150 miles, 100 miles, 100K, 50 miles, 50K, and 10 miles, with both daytime and nighttime options. The course is a scenic 10.48-mile loop through the pine barrens of Long Island, o..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..

The Gemstone Sparkle Sprint 5k is a community-focused trail running event held at Gemstone Farm in Wilton, Connecticut. Scheduled for October 11, 2025, this scenic 5k trail run welcomes participants of all abilities, encouraging runners and casual walkers alike to dress in sparkly attire and enjoy t..

The Paine to Pain Trail Half-Marathon is a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..

The Never Stop Running Foundation Great Pumpkin Dash Trail 5K is a scenic trail run/walk held at Blydenburgh County Park in Smithtown, NY. Scheduled for October 12, 2025, this event features a 5K course that winds through shaded trails combining dirt roads and hard-packed surfaces with some sandy sp..

The Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers a challenging trail running experience with marathon, half marathon, 10K, and 5K distances. The course features steep ascents and descents on ski mountain trails, including the Wildwood, Timber, Pine, Laurel,..