Paine to Pain Trail Half Marathon

SEP
26
2027
A single-loop trail half marathon through five Westchester parks, mostly on dirt and roots, chip-timed with three aid stations and a 3 hour course limit.
Sun 26 Sep 2027
Half Marathon

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Paine to Pain Trail Half-Marathon

The Paine to Pain Trail half-marathon is a single-loop trail race in lower Westchester County, New York, that passes through five different parks. The course keeps runners on a variety of natural surfaces—about 90% on dirt, rocks, and roots—and largely in the shade of the woods. Runners do not repeat the same trail twice and the route includes roughly 950 feet of vertical gain, finishing at the same elevation as the start.

The event is chip-timed and runners begin in multiple waves to reduce trail congestion. There is a 3-hour course limit measured from the start of the final wave. The race is semi-supported with three water and aid stations located at about Miles 4, 7.5, and 11; medical support is available at stations and at the finish. Toilets are provided at the start, Mile 7.5, and the finish.

Registration for 2027 opens in spring 2027 and follows tiered pricing with listed early and later rates; there is no race-day in-person registration. Members of the local running club and military veterans receive a discount during specified registration windows. Packet pickup is available in advance at a local running store or on race morning at the Thomas Paine Cottage staging area; a bag drop near the start transports bags to the finish.

Headphones and dogs are not permitted on the course. Awards include engraved tankards for overall top three and age-group awards by chip time. Visit the organization's website for the most recent information.

Events nearby

A family friendly 5K trail run or walk at Bethpage State Park on November 14, 2026 with a free kiddie dash, post race refreshments, finisher photos and a virtual option.
A scored cross country 5K at Van Cortlandt Park on November 15, 2026, open to ages 8 and up, run on wooded trails with on-site awards and race-day amenities.
A community 5K at Inwood Hill Park on November 26, 2026, with proceeds to the Inwood Food Pantry, personalized bibs by 11/1, and medals for the first 700 finishers.
A community 5K run and virtual option at Alley Pond Park on November 26, with a free kiddie dash, on-course refreshments, and proceeds supporting the Never Stop Running Foundation.
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