Trail Running calendar near Shandaken 2025-2026

The Tunxis Trail Ultramarathon, held in Burlington, Connecticut, features challenging and technical trail races on the Tunxis Trail system, part of the Blue Blazed hiking trails. The event offers shorter distances this year, including an 8K (5 miles) and a 5K (3.1 miles), with staggered start times...

The Water Gap 50k and 25k is a scenic trail running event held in Milford, Pennsylvania, within the Delaware Water Gap National Recreation Area. The race courses follow the McDade Trail, a 32-mile route featuring a mix of rail-trail style cinder paths and singletrack terrain. Known for its rolling,..

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 NJ Trail Series One Day is a multi-day ultrarunning event held at the Sussex County Fairgrounds in Augusta, New Jersey. Scheduled from October 2 to 5, 2025, it features a variety of race options including 72, 48, 24, 12, and 6-hour timed races, as well as marathons and 50K distances. The course..

The Flutters and Foliage Endurance Run, held in Cohoes, NY, is a unique ultra running event supporting Flutters of Hope, a nonprofit aiding individuals and families affected by eating disorders. Now in its third year, the race features multiple endurance challenges including 1-hour, 3-hour, and 6-ho..

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 Trailwagger is a running event held at Gilbert Lake State Park in Laurens, NY, featuring scenic trails and fall foliage. The race offers four divisions to accommodate various skill levels: a 3-mile run/walk on paved roads and trails, a mostly trail-based 5-mile run showcasing ponds and creeks, a..

The Costumed Creature Crawl 5K Trail Run/Walk is held at Van Scott Nature Reserve in Beach Lake, Pennsylvania, supporting Pregnancy and Infant Loss Awareness Month. Scheduled for October 11, 2025, participants can run or walk the 5K trail in person or virtually. The event welcomes all ages, with spe..

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

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 18 October 2025. You can run 3 miles.

Run The Farm - Katonah is a scenic 5-mile trail race held at Muscoot Farm in Katonah/Somers, New York. Scheduled for October 19, 2025, the event features a main 5-mile race open to participants aged 6 to 108, along with two kids' races: one for ages 7-12 and another for children 6 and under. The rac..

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

The Malta Trail Race in Malta, NY, hosted by the Roundabout Runners Club, offers 2k, 3k, and 5k trail running events set in the scenic 100 Acre Woods. The course starts at the Luther Forest Athletic Fields and features well-maintained trails, mostly covered in stone dust and wide enough for comforta..

The Big Bear Squatchtoberfest is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Organized by Sassquad Trail Running in partnership with the New York-New Jersey Trail Conference, it features a half marathon (13.1 miles) and a 10K race. The courses are technical wit..

The Veeder Tree Farm 5K is a running event held in Earlton, New York, at 1235 High Hill Rd. Scheduled for October 19, 2025, the race offers multiple categories including a 5K, 5K Trail Run, and combinations thereof, with options for students as well. The course features a mix of trail and traditiona..

The Fall Back Into The Trails Series, held at Red Wing Recreation Area in Lagrangeville, NY, offers challenging trail races including a 100K, 50K, and 10K. The 50K consists of five 10K loops with approximately 5,000 feet of elevation gain, while the 100K features ten 10K loops with about 1,000 feet..

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 that includes single track and farm trails, offering a scenic and community-focused atmosphere. Participants can cho..

The Saratoga Stryders Fall Back 5 Mile Trail Race is held annually at Saratoga Spa State Park in Saratoga Springs, NY. This challenging 5-mile course features a mix of hills, ridges, single-track trails, wide paths, paved sections, grassy areas, and even a stair climb near SPAC, offering runners a d..

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, offers both marathon and half marathon distances through Rockefeller State Park. The single-loop courses feature rolling hills with scenic views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, streams, forests,..