Trail Running calendar near Ansonia 2025-2026

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..

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..

The Paine to Pain Trail Half-marathon is scheduled for Sunday, October 12, 2025, in New Rochelle, Westchester County, New York. The race is organized by NewRo Runners and is part of the Trail Mix Series, a group of seven trail races in Westchester County, NY and Fairfield County, CT. The event uses..

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 Fred Torres Memorial 5K is the 12th annual charity race at Garrett Mountain in Woodland Park, New Jersey. The live event features a 5K run on a championship cross-country course and a 2-mile walk, with a virtual 5K option for remote participants. Family-friendly events include a Tot Trot and a 1..

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..

The Mt. Tom Trail Race takes place on October 18, 2025, with the start/finish and parking at Bray Lake in Mt. Tom State Park. The event is a nonprofit fundraiser that supports the Kestrel Land Trust. Registration fees are non-refundable and non-transferable. Check-in is held one hour before each ra..

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

Big Bear SquaTCh South, a Sassquad Trail Running event in Harriman State Park, Tuxedo, New York, features a challenging pair of trail races: a 13.1-mile half marathon and a 10K, starting and finishing at Powerhouse Park. The single-loop courses are rugged and technical, with 2,200+ ft of gain on the..

Bimblers Bluff 50K is an off-road ultramarathon in southern Connecticut, starting at Guilford Lakes School in Guilford. The 50-kilometer course weaves through interconnected woodland preserves, using rolling forest roads and rocky single-track. The route is notable for not requiring repeated loops,..

FALL Run The Farm is a trail race held at Muscoot Farm in Katonah/Somers, New York on October 19, 2025. The main event is a 5-mile trail race. The event program also includes two kids races: one for ages 7-12 and one for ages 2-6. The main 5-mile race is open to ages 6 through 108. The event is or..

The Grills Trail Run takes place on Saturday, October 25, 2025, at Grills Preserve, 198 Bowling Lane, Westerly, Rhode Island. It is the third race in the Westerly Track & Athletic Club (WTAC) Fall Trail Race Series. The event offers two distance options: 10 Mile 10K Both courses start and fin..

Cheshire Community YMCA 5K Harvest Trail Run in Cheshire, CT, is a race around Ives Farm. The all-ages event winds through fields and trails on the farm, starting and finishing at the remodeled barn. Proceeds support the YMCA’s Cheshire community programs and the Cheshire Land Trust’s revitalization..

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..

RACE FOR THE GREENWAY 5K RUN / WALK takes place at Hallock State Park in Riverhead, NY. The mostly flat off-road 5K course weaves through parkland with views of beaches, vineyards, ponds, and forests, featuring loose gravel and grass underfoot. Runners and walkers of all abilities are welcome.After..