Trail Running calendar near Northport 2025-2026

Winding Trails TRAIL RUNNING Series #4 is a five-race Tuesday-night trail series in Farmington, CT. Race #4 runs from Aug 26 to Sep 23, 2025, offering 5K or 10K options on a roughly 3-mile loop. Check-in and a rolling start take place at Winding Trails, 50 Winding Trails Drive.Registration is availa..

The event is a corporate 5k run/walk taking place on Tuesday evening, September 16, 2025, at Hudson River Park - Pier 84 (West 44th Street), New York, NY 10036. The program includes pre-race packet pickup and company gatherings on the westernmost part of Pier 84, the 5k out-and-back run/walk on the..

Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey. The event offers a true Trail Festival with distances spanning from a 1-mile kids race to 100 miles, plus 100K, 50 miles, 50K, and a 36-hour format (with lightweight and heavyweight rucking divisions). The course co..

Angevine Farm Half Marathon takes place in Warren, CT, at Angevine Farm as part of the Angevine Farm Trail Festival. The course starts at the farm, loops on farm trails, enters Wyantenock State Forest and the Mattatuck Trail, delivering mostly technical but runnable single- and double-track terrain..

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 Cockaponsett Trails to a Cure is a trail running event held in Chester, Connecticut, within the Cockaponsett State Forest. Participants can choose between a 4-mile or a 9-mile race, with the shorter distance covering the first part of the longer course. The trail features natural terrain includi..

Winding Trails TRAIL RUNNING Series #5 is a Tuesday night event at Winding Trails in Farmington, Connecticut. The 2025 edition runs five races from August 26 through September 23, with a choice of 5K or 10K on an approximately 3-mile loop. Check-in and rolling start occur in the early evening at 50..

The Caldwell Cougar Chase XC 5K & 8K is a cross-country running event held at Garret Mountain Reservation in Woodland Park, New Jersey. Scheduled for September 26, 2025, it features a women's 5K and a men's 8K race on a rolling course that includes trails, hills, gravel, dirt paths, grass sections,..

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...

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..

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..

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..

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..

The Fat Sass Switchback Challenge is a trail running event held in Millburn, New Jersey, at the South Mountain Reservation's Locust Grove Picnic Area. Scheduled for October 5, 2025, it features a challenging 1-mile loop course with 300 feet of elevation gain, including steep climbs and technical, ro..

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..

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..