Trail Running calendar near Kent 2025-2026

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..

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...

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..

Front Runners New York's Cross Country 5K returns to Van Cortlandt Park in the Bronx for its 22nd annual fall meet. The Run/Walk begins near the Tortoise & Hare Sculpture, with bib pickup guided by FRNY volunteers. Supported by the Tom Cook Fund, race-day amenities include on-site registration, swag..

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 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..

Chasing Ciara's Light 5K/12K Trail Race 2025, held at Great Hollow Lake in Monroe, CT, offers timed 5K and 12K trail races along a scenic course. Sanctioned by USATF and spectator-friendly, it features multiple spots for cheering. A Kids Fun Run provides additional family-friendly activity.The cours..

CT Donut Run is a 31.5-mile charity group run in Connecticut, presented as a long, donut-filled endurance experience rather than a traditional race. The route centers in West Hartford and visits several donut stops, including locations in Newington, Berlin, Wallingford, and North Haven, finishing in..

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 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..

Set in Montebello, New York, the KMT Fall Foliage Frenzy is a trail-running event featuring 3-hour and 6-hour timed races. Runners tackle a challenging 2.33-mile loop with about 660 feet of vertical gain, weaving through Kakiat Park against the backdrop of Harriman State Park and the Hudson Valley’s..

NipMuck Trail Marathon, in Ashford, CT, features two options: the original NipMuck Trail Marathon (26.4 miles) and a two-person NipMuck Relay. The race uses a 13-mile middle segment of the Nipmuck Trail, running south to Route 44, back to the start, then north to Boston Hollow before finishing at Pe..

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..

IBBC Trail Classic 5k and Kid's Trail Run presented by Peace, Love, Trails takes place in Irvington, New York, with the event centered around the Irvington Woods trail system near 40 N Broadway. The lineup includes a 5k Trail Run/Walk through scenic woodland paths and a 0.6-mile Kid's Trail Run for..

Tesla Hertz Run is an ultrarunning event in Rocky Point, New York, offering multiple distances on a single Long Island course: 150‑mile, 100‑mile, 100K, 50‑mile, 50K, a 10‑mile, and a night-time 10‑mile option. The course features a scenic 10.48‑mile loop through pine barren terrain, with two aid st..

Forbidden Forest 30 Hour Ultra Run takes place in Roosevelt Forest, Stratford, Connecticut, October 11-12, 2025. Runners choose a personal challenge on a 2.23-mile loop that weaves through roots, rocky terrain, and a standout hill dubbed "OMG." Competitors can tackle 26.2M, 50K, 50M, 100K, 100 Miles..

Gemstone Sparkle Sprint 5k is a community trail run in Wilton, Connecticut, on Gemstone Farm (144 Huckleberry Hill Rd). The second annual event offers a scenic 5k trail course suitable for all abilities (strollers not allowed on the course) with a festive sparkly theme inviting participants to dress..

Mohawk Mountain Race, at Mohawk Mountain Ski Area in Cornwall, CT, offers 5K, 10K, half marathon, and marathon distances. The course turns a ski mountain into a challenging trail race, with steep climbs and descents and views of fall foliage. The 5K loop climbs the left side via the Wildwood and Tim..

NSRF Great Pumpkin Dash Trail 5K is a Halloween-themed run/walk held at Blydenburgh Park in Smithtown, New York. The scenic, shaded course weaves through dirt roads and hard-packed trails with a few sandy spots, offering a non-technical trail experience suitable for first-time runners; strollers and..