Trail Running calendar near Pittsfield 2025-2026

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..

The Buck 50 is a challenging 50-kilometer ultramarathon held in Kattskill Bay, New York, along the scenic southern Adirondacks near Lake George. The course features rugged, remote trails that traverse four of Lake George's tallest peaks, including Buck Mountain, Sleeping Beauty, Black Mountain, and..

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..

The Midstate Massive Ultra Trail is a multi-distance, point-to-point trail race organized by New England Race Events in New Ipswich, New Hampshire, with routes extending into nearby Massachusetts and Rhode Island. It offers 100-mile, 50-mile, and 50-kilometer options, tracing the historic Midstate T..

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..

The North Face Race to the Summit is a mountain-top running event held at Stratton Mountain in Stratton, Vermont. The course covers about 2.18 miles with a 2,003-foot vertical climb, delivering a steep uphill challenge amid alpine terrain. The race is timed with live results and leaderboards, with o..

Mt. Tom Trail Race takes place in Mt. Tom State Park in Massachusetts, with parking at Bray Lake.The event offers multiple distances: a 25k solo, a 25k two-person relay, a 10k, and a 5k fun run/hike, all on rugged single-track trails within the park. The 25k course features about 3,600 feet of eleva..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run/walk hosted by the Wolcott Lions Club in Wolcott, Connecticut. The race unfolds on the scenic, flat Mill Pond Trail at Woodtick Recreation, 201 Nichols Road. This community event benefits local charities and the Tom Centinaro Lions scholarshi..

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..

The Veeder Tree Farm 5K is a running event held in Earlton, New York, at 1235 High Hill Rd. Scheduled for October 19, 2025, the race offers multiple categories including a 5K, 5K Trail Run, and combinations thereof, with options for students as well. The course features a mix of trail and traditiona..

Book It for Books 5k & 10k is a charity running event at Lake Accotink Park in Springfield, VA, benefiting Reading is Fundamental of Northern Virginia (RIF NOVA). The weekend features a 1-mile fun run, a 5k trail out-and-back on the lake’s south side, and a 10k course that runs out-and-back on the n..

Fall Back Into The Trails Series returns to Red Wing Recreation Area in Lagrangeville, NY for its 9th annual edition on November 1-2, 2025. The event offers three races: 100k (10x10k loops with about 1,000 ft of gain per lap), 50k (5x10k loops with about 5,000 ft total gain), and 10k (about 1,000 ft..