Trail Running calendar near Monroe 2025-2026

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 time..

Event overview The IronHike Endurance Series takes place in Cornwall, Connecticut, at Mohawk Mountain Ski Area from October 2 to October 5, 2025. The series is organized by IronHike Endurance Productions LLC, a US military veteran-owned bus..

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 N..

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 Fu..

The CFA Trail 5K & Children's Fun Run for Mental Health is a timed trail running event held at Deans Mill Farm in Stonington, Connecticut. Participants can choose between a 5K trail run or a fun run for children aged six and under. The race..

Event details The Run for the Pumpkins Trail Run is scheduled for Saturday, October 4, 2025, at Bradford Preserve, 199 Bradford Road, Westerly, RI. It is the second race in the WTAC Fall Trail Race Series (4 races). A 10% per-event discount..

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..

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 fla..

NipMuck Trail Marathon in Ashford CT offers 26.4 miles of rugged singletrack with rocks, roots, mud and wood bridges. Run solo or in a two person relay and help support Connecticut trail stewardship.

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 a..

Tackle a steep, technical 1 mile loop of switchbacks in Millburn with 5K, 3HR or 6HR loop options. This rugged trail fundraiser supports Bigger Than The Trail and challenges runners on rocky singletrack.

Event details The KMT Fall Foliage Frenzy takes place on October 5, 2025, in Montebello, New York. The event is held at Kakiat Park, near Harriman State Park, at 668 Haverstraw Rd. Registration closes on October 4. Course and awards The eve..

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 throu..

Take on the Tesla Hertz Run in Rocky Point NY with races from 10 miles up to 150 miles on scenic Long Island pine barrens trails. Generous cutoffs, lively aid stations, and night race options make this a welcome challenge for beginners and..

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)..

Run 30 haunting hours beneath a canopy of autumn leaves in Stratford CT on a rugged 2.23 mile loop with roots, rocks and one memorable climb. Limited to 50 runners, chase miles and earn a stunning 100 mile buckle.

Event details 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..

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 par..

Goodwin Trail Challenge (October 12, 2025) The Goodwin Trail Challenge is a registered mountain bike event held on October 12, 2025. Registration is required through BikeReg and includes a donation to East Haddam Land Trust that provides a..

Join the Great Pumpkin Dash Trail 5K at Blydenburgh County Park on Oct 12 for a fun, scenic trail run with an in person or virtual option and a free Kiddie Dash. Proceeds support the Never Stop Running Foundation.