Trail Running calendar near Sleepy Hollow 2026-2027

A scenic and classic spring run for athletes aged 30+. Choose between the 10K and 5K distances on a mostly flat loop course through woods and around Birchwood Lake in Mountain Lakes. Be prepared for varied surfaces including paths, trails,..

Experience the Leatherman's Loop 10k trail race at Ward Pound Ridge Reservation in New York. Entry is managed via a lottery system for this USATF sanctioned spring event through the local woods.

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

Experience a technical 5 mile trail run through 250 acres of scenic green space in Killingworth. Navigate rocky terrain and elevation shifts at the Deer Lake Outdoor Center with awards for multiple age categories.

Join the Your Story Matters Falcon 5K in Oak Ridge for a scenic trail run or a vibrant Youth Color Run. Support mental health awareness while enjoying a day of community activities and local giveaways.

The XC Summer Series offers weekly Tuesday evening 5K cross country races in Parsippany's Central Park. The thirteen race series welcomes all ages and abilities, with chip timing and post race refreshments. Participants can register for the..

An ultramarathon in Van Cortlandt Park featuring an initial flat lap plus ten cross country loops, stocked aid stations, drop bag access, and finisher awards including a medal, singlet, meal and post race beer.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

The first annual Lawrence Hopewell Trail 5K supports a 20-mile community trail. The race course passes by two lakes and the historic Hunt House. A non-competitive one-mile Fun Run is also offered for all paces.

Experience the beauty of the Shawangunk Mountains with a 50 mile ultra, a trail marathon, or a team relay. Enjoy well maintained carriage roads and an 18 hour cutoff in this premier fundraising event for Mohonk Preserve.

Trail races at Bear Mountain State Park on May 2, 2026 include 10K, half marathon and 50K over singletrack with technical sections, rolling climbs, tree cover, rocky and muddy terrain and occasional stream crossings.

Run a flat one mile course in Van Cortlandt Park while wearing your own inflatable costume. This unique Bronx event supports charity and takes place during a local ultramarathon for a high energy atmosphere.

Experience a 5K trail run through Jacobsburg State Park in Nazareth. Support the Wreaths Across America project while competing for speed or participating in patriotic and holiday themed costume contests.

Experience one of the most technical and elevation dense trail races in the Northeast. Tackle steep climbs and rugged single track through the scenic terrain of Beacon, New York.

Join the fifth annual Green Traill event in Easton, PA. It features a timed 5K run, a 2-mile walk, and a free Kids Fun Run. The volunteer-led event supports the preservation of Easton Cemetery.

A technical trail 50K in New Haven on blue-blazed trails with about 6,350 feet of climbing and multiple aid stations. Entry is by waitlist and requires a recent trail 50K qualifier; no crews or pacers are allowed.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

This community trail run on Clausland Mountain honors caregivers and supports mental health and sobriety causes. Participants take on a 3.75-mile historic course, receiving a medal in an event focused on gathering, not competition.

A dual-event day featuring a Family Color Run and a 5K Trail Run on May 9, 2026, in Hamden, CT. The first 100 to pre-register get a special giveaway, with water stations available for all participants.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..