Paine to Pain Trail Half Marathon
New Rochelle, United States • 11 Oct 2026
Paine to Pain Trail Half-Marathon
The Paine to Pain Trail Half-marathon is an annual trail race held in lower Westchester County, New York. The 18th edition is scheduled for Sunday, October 11, 2026 (tentative). The event is hosted by NewRo Runners and is part of the Trail Mix Series, which showcases seven trail races in Westchester and Fairfield counties.
Course and location
The race is a single large loop that passes through the woods and trails of five different parks. Runners do not repeat the same trail and spend about 90% of the course on dirt, rocks, and roots under tree cover. Some trail sections are hidden from public view. The route begins at the Thomas Paine Cottage in New Rochelle and finishes at New Rochelle High School, across the street from the start. The area features a variety of wildlife, including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, and bald eagles. Visit the organization's website for the most recent information.