Trail Running calendar near Great Barrington 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..

All of the Above Trail Fest is held at Northfield Mountain Recreation Area in Northfield, Massachusetts. A collaboration between Beast Coast Trail Running and The Venture Out Project, the festival centers on inclusivity for queer and transgender runners and their allies, celebrating people over boxe..

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..

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 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...

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..

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..

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...

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..

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..

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds more challenging rolling singletrack and elevation. Runners..

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..