Trail Running calendar near East Hampton 2026-2027

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

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.

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

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

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

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.

This 50k trail run connects Connecticut's technical Regicides and Quinnipiac Trails. The challenging out-and-back course features significant climbing and a strict 10-hour cutoff. The event does not allow pacers or crews and enforces interm..

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

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.

Experience the varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

Test your limits in Connecticut's original last person standing race on the rugged Ragged Mountain trails. Complete a 3.11-mile loop each hour until only one runner remains. A headlamp is required for the night, and all proceeds support loc..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Experience the beauty of the Ashuwillticook Rail Trail with a marathon, half marathon, or 8K race. This annual event includes USATF certified courses, finisher medals, and a dedicated kids run for families.