Paine to Pain Trail Half Marathon
New Rochelle, United States • 11 Oct 2026
Paine to Pain Trail Half-Marathon - New Rochelle, New York
The Paine to Pain Trail Half Marathon is an annual trail race held in lower Westchester County, New York. The event is presented as a single large loop that passes through the woods and trails of five different parks in the area. The course begins at the Thomas Paine Cottage in New Rochelle and finishes at New Rochelle High School, which is located across the street from the start.
Runners spend approximately ninety percent of the route on unpaved surfaces, including dirt, rocks, and roots, and much of the course runs in the shade of the woods. Many sections of trail are not visible from public roads and support diverse wildlife. Species reported along the route include deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, and bald eagles.
The race is organized by the local NewRo Runners group and is included in the Trail Mix Series, a collection of seven trail races in Westchester County, New York and Fairfield County, Connecticut. The listing notes the event as the 18th running and gives a tentative date of Sunday, October 11, 2026. Visit the organization's website for the most recent information.