Trail Running calendar near Windham 2026-2027

A 53-mile Catskills ultramarathon with about 15,000 feet of climb, technical trail sections, nine aid stations and a 23-hour cutoff. The point-to-point route starts near Windham and finishes in downtown Phoenicia.

Operation WOODSTOCK on June 20, 2026 in Elka Park, NY is a 14.5 mile load bearing event with 5,210 ft elevation gain and a 20 lb dry pack. Entry is listed at $105 plus $7.35 tax.

A looped trail event at Lawson Lake Park on June 20, 2026, offering 2.5M, 5M and a one hour format. Entry includes a shirt and post race food; individual and team awards recognize top finishers and most laps completed.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

TSR Trail Race is a loop-format trail run on June 21, 2026, in Adams, MA, featuring hand and machine built singletrack with climbs, descents, and a gravel meadow loop; proceeds support Thunderbolt Ski Runners' trail stewardship.

A five‑race 5K trail series at Camp Saratoga across summer Mondays, capped at 375 entries for the series. Individual races or a full series package are available and proceeds benefit the Wilton Wildlife Preserve & Park.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24, 2026, over unpaved carriage paths with chip timing and commemorative towels for all finishers.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support the Pawling Recreation Department.

A trail event at Red Wing Recreation Area on July 5, 2026, offering 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, and awards for top finishers.

Part of the Shawangunk Runners summer series, this week features a 4.7 mile Undercliff Overcliff loop plus kid races, held at Trapps Bridge with parking at Mohonk Preserve West Trapps and no registration fee.

Notchview Ultra is a multi day running event July 10-13, 2026 in Windsor, MA featuring fixed distance and timed races on a 1.9 mile loop with an aid station, camping logistics, and charity fundraising.

A 5K obstacle mud run in Albany on July 12, 2026 at Harley Rendezvous Classic Inc. The event offers standard and VIP ticket options with race items, rinse stations, and photos, and donates to the National Breast Cancer Foundation.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

A 55K self-supported trail ultramarathon in New York's Adirondack Park along the Northville Placid Trail. Technical terrain with about 3,300 feet of gain; registration requires a qualifying race and includes a shirt and two meals.

Two trail-focused races at Beartown State Forest in Great Barrington, MA: a 5-mile loop around Benedict Pond and a roughly 13.5-mile half with significant climbing and technical terrain. The event is cupless with limited parking and shuttle..

Part of the Shawangunk Runners summer series since 1974, the Blueberry Run in Kerhonkson features a 4.1 mile loop around Lake Minnewaska plus shorter kids races, with parking at Minnewaska State Park and no registration fee.

A third annual cross country event in Warwick, NY on July 25, 2026, featuring a mass-start 5k and a non-timed 400 m Kids Dash with finishers ribbons.

A 30 km singletrack mountain race in the Catskills on July 26, 2026 with about 4,800 ft of climb and a six hour cut off. The remote route has limited aid, wave starts, and entry requires qualifying standards.

A trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.

A five mile trail race on the Gurney Lane Trails in Queensbury, NY featuring single track terrain, chip timed results, age group awards, a post race celebration and proceeds benefiting the Under the Woods Foundation.