Trail Running calendar near Shandaken 2025-2026

The Red Wing Trail Challenge, held at Red Wing Recreation Area in Lagrangeville, NY, offers two trail race distances: a challenging 60K with approximately 6,600 feet of elevation gain, and a 15K featuring about 1,650 feet of gain. The 60K consists of four laps of a 15K loop that includes varied terr..

The Undercliff/Overcliff race is the first event in the 52nd Summer Series hosted by Shawangunk Runners, held in Gardiner, New York. This iconic 4.7-mile loop race starts and finishes at Trapps Bridge, with parking available at the Mohonk Preserve West Trapps entry. Since 1974, the series has showca..

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with aid sta..

The Second Annual Orange Runners Club Summer Sizzle XC5k is a cross country running event held in Warwick, New York, at the Rich Furst Sanfordville Elementary School XC Course. This 5k race, rooted in teamwork, dedication, competition, and fun, takes place on a course known for its rich cross countr..

The Newbsanity Extreme Ravine Trail Race, held in Binghamton, NY, offers a challenging trail running experience on the southern trail system of the Newbsanity Adventure Center. Participants can choose from a 5K single loop, a 15K race consisting of three loops, or a demanding 12-hour endurance event..

The People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

The Landis Arboretum 5K Forest Run, held in Esperance, NY, is a scenic cross-country race through the arboretum’s forests and meadows, offering beautiful views of the Schoharie Valley. This rolling 5K course is part of the Route 20 Challenge Series and is USATF sanctioned. The event features chip ti..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

The Thunder Chicken Squatch is a trail running event held at Stokes State Forest in Branchville, New Jersey. Scheduled for August 10, 2025, it offers multiple race distances including a challenging 17-mile run, a 10K, and a 5K, with additional 10K rucking divisions featuring lightweight (15 lbs) and..

Climb It For Climate is a mountain trail running event held at Belleayre Mountain Ski Center in the Catskill Mountains, New York. Participants can choose between a challenging 25K course, approximately 15 miles with 5,000 feet of elevation gain and descent, or a shorter 8K course of about 5 miles wi..

The Tappen Brook 5K, held in Bridgewater, Connecticut, is an annual trail running event hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Set in the scenic Bridgewater Town Park, the course features newly developed trails winding through forested woodlands with gentle h..

The Fabulous Fahnestock Trail Races, held in Cold Spring, NY, offer runners a choice of 50K, 25K, and 5.5-mile distances through scenic Fahnestock State Park in the Hudson Valley. The course features a mix of runnable dirt roads and technical single-track trails, with challenging climbs, flowy desce..

The Hook Mountain Ultra is a challenging 51.7-mile trail run held in Upper Nyack, New York, featuring 10,928 feet of elevation gain. The course includes one 5.7-mile small loop followed by four 11.5-mile big loops, all starting and finishing at Nyack Beach State Park. Runners begin with a steep 1.6-..

The Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap. The course includes uphill and..

The Thacher Park Trail Running Festival, established in 2014, takes place at Thacher State Park in Voorheesville, NY. This scenic event offers participants a choice of four race distances: 10K, 13.1M, 26.2M, and 50K, allowing runners to experience the park's beautiful trails. The festival promotes a..

Raptor Ridge Presented by Peace, Love, Trails (formerly the Sanctuary 6.5) is a challenging 6.5-mile trail run held at the scenic Westmoreland Sanctuary in Mount Kisco, New York. The race takes participants through the sanctuary's beautiful and rugged trails, spanning 669 acres with 8.5 miles of hik..

The Salt Springs Field, Forest & Falls Trail Race, held in Montrose, Pennsylvania, offers a rugged trail running experience through old-growth forests with stunning scenery. In its 13th year in 2025, the event features three distances: 5K, 10K, and a challenging 50K race. The 5K is mostly trail, whi..

The Macedonia Trail Race, held annually in Macedonia Brook State Park in Kent, Connecticut, offers a unique trail running experience with lush forest single tracks, challenging climbs and descents, and stunning viewpoints including Cobble Mountain with views of the Catskill Mountains. Now in its 7th..

The Brookfield Classic is a trail running event held in the scenic Charles E Baker State Forest in Brookfield, New York. It offers three race distances: a 5K for beginners or casual runners, a family-friendly 15K loop combining truck and horse trails suitable for walking or running, and a challengin..

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..