Paine to Pain Trail Half Marathon

Paine to Pain Trail Half-Marathon

The Paine to Pain Trail Half-Marathon is a single-loop trail race that travels through the woods and trails of five parks in lower Westchester County, New York. The course routes runners from the Thomas Paine Cottage area in New Rochelle to New Rochelle High School, with the finish located across the street from the start. The event is presented in New Rochelle at North Avenue and Broadview Avenue and is about four train stops north of Midtown Manhattan.

The course stays on natural surfaces for most of the distance, with roughly 90% on dirt as well as rocks and roots, and runners spend much of the route in the shade of the woods. The loop design means participants do not run the same trail twice. Many sections of trail are hidden from public view and pass through areas inhabited by a variety of wildlife, including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, and bald eagles.

The race is part of the Trail Mix Series, a collection of seven trail races in Westchester County, New York and Fairfield County, Connecticut. The event is listed as the 18th annual running and has a tentative date of Sunday, October 11, 2026. Visit the organization's website for the most recent information.