Trail Running calendar near Roxbury 2025-2026

Located at Lakeside Park in Pawling, New York, the Pawling 24 Hour Trail Running Festival is the sixth edition of the endurance event, offering 24-, 12-, 6-, and 3-hour races (including a 12-hour night start). Runners tackle a 1.68-mile loop made up of pavement, grass, and single-track, with about 1..

Brookfield Classic takes place in Brookfield, New York, deep in the woods of the Charles E. Baker State Forest. The event features three trail distances: 5K, 15K, and a 50K Ultra Marathon.The 5K offers a beginner-friendly option to ease into trail running. The 15K traverses a loop over a mix of truc..

Shawangunk Ridge Trail Run (SRT) unfolds along the Shawangunk Ridge in the Hudson Valley, offering three divisions: 70-mile, 30-mile, and 1/2 marathon, spanning from High Point Monument in NJ to Rosendale, NY. The route winds through hills, wetlands, pine barrens, sky lakes, waterfalls, and conglome..

Rensselaerville Ramble Trail Run & Walk is a fundraising event held in Rensselaerville, New York. The Ramble starts and ends at the Huyck Preserve's Eldridge Research Center and guides participants through the Preserve's forested trails. Runners and walkers can choose from 2-mile, 5-mile, or 8-mile..

Connor's Way Scenic Memorial 5-Mile Run/Walk takes place in Hinckley, New York, in the foothills of the Adirondacks. The course spans five miles on a scenic, wooded trail with sections on seasonal roads and trails. The event emphasizes celebration of life, nature, and community while supporting Conn..

Angevine Farm Half Marathon is part of the Angevine Farm Trail Festival in Warren, CT, hosted by Steep Endurance. The event offers a Half Marathon plus an 8-Hour option and a 5K/5K Canicross, all on scenic farm and forest trails. The Half Marathon begins at Angevine Farm, runs a 1.7-mile farm loop,..

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 Cat's Tail Trail Marathon is a challenging 26-mile point-to-point trail race held in the Slide Mountain Wilderness Area of the Catskill Mountains, New York. Featuring nearly 7,000 feet of elevation gain, the course offers rugged terrain with rocky, technical climbs and descents, alongside stunni..

Race to the Face 5K is a community-oriented running and walking event in Norwich. In 2025, the event enters its fourth year. The course starts on a road in downtown Norwich, switches to trail, then returns to the road and downtown, accommodating runners, walkers, and hikers and even friendly dogs.Pa..

Water Gap 50k and Half takes place in Milford, Pennsylvania, within the Delaware Water Gap National Recreation Area. The event offers 50K and 25K distances, with the McDade Trail serving as the course—a 32-mile point-to-point route through the Gap, mixing rail-trail cinder paths with rolling singlet..

IronHike Endurance Series brings a mountain-style challenge to Mohawk Mountain Ski Area in Cornwall, Connecticut. The Fall 2025 edition runs across October 2–5 and offers six self-paced events ranging from 12 to 84 hours. Core distances include Olympus Mons Ultra (152+ miles, about 72,590 ft of elev..

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..

Michael J. Pitney Farm Run takes place at Pitney Meadows Community Farm in Saratoga Springs, NY. The event features a 5K community run and a Youth Fun Run (.5 miles).The course is a mixed-surface, grass and stone-dust trail that is primarily flat with a few gentle rollers, and has no road crossings...

Iron Hike’s Fall Double Kuwohi Trail Marathon Plus Relay is a weekend endurance event set at Mohawk Mountain Ski Area in Cornwall, Connecticut. The race covers 28+ miles with 13,685 feet of elevation and is designed to be completed within a 24-hour window. Participants have the flexibility to run, h..

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..

Costumed Creature Crawl 5K Trail Run/Walk is an in-person and virtual race in Beach Lake, Pennsylvania, at the Van Scott Nature Reserve of the Delaware Highlands Conservancy. It offers a 5K trail run or walk for adults, plus options for ages 6-15 and free Crawlers age 0-5. Trails are not stroller-fr..

Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, CT, is a Steep Endurance trail event offering 5K, 10K, Half Marathon, and Marathon distances. The course climbs the mountain on Wildwood and Timber Trails, then traverses Pine, Laurel and Deer Run Trails, before a summit return via..

UR Skeleton Run takes place at Deerfield Town Park in Deerfield, NY. The event includes three races: Skeleton Run 5K (3.1 miles), Skeleton Community Run (1.5 miles), and a Kids Quarter Mile for ages 3–12. Runners traverse the park’s Wilderness trails, with organizers noting the course can get muddy..

Malta 2K, 3K, 5K Trail Race in Malta, New York, is organized by Roundabout Runners Club. The event begins at Luther Forest Athletic Fields near 30 Rocket Way and runs through the well-maintained trails of 100 Acre Woods, featuring wide stone-dust paths and sections of soft ground that immerse runner..