Paine to Pain Trail Half Marathon
New Rochelle, United States • 11 Oct 2026
Event overview
Paine to Pain Trail Half-Marathon is a trail race held in New Rochelle, Westchester County, New York. The 2026 edition is scheduled for Sunday, October 11, 2026 (tentative) and is listed as the 18th annual running. The event is organized by the local running club NewRo Runners and is part of the Trail Mix Series, a group of seven trail races in Westchester County, NY and Fairfield County, CT.
Course and location
The race is a single large loop that passes through the woods and trails of five different parks in lower Westchester County. The course starts at Thomas Paine Cottage in New Rochelle and finishes at New Rochelle High School, across the street from the start. Runners do not repeat the same trail segments and spend about 90% of the route on dirt, rocks, and roots under tree cover.
Trail features and wildlife
Many sections of the course are on trails that are not visible from public roads. The area hosts a variety of wildlife, including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, and bald eagles. The terrain includes natural trail surfaces with exposed roots and rock.
Registration
The listed entry fee for the Paine to Pain Trail Half-Marathon is $55 for the main event. Registration for the 2026 race opens April 22, 2026; a separate free event to claim NewRo club membership has a registration opening date of May 4, 2026. Visit the organization's website for the most recent information.