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 a single-loop trail race scheduled for Sunday, October 11, 2026 (tentative) in New Rochelle, Westchester County, New York. The course winds through woods and trails in five different parks in lower Westchester County, so participants do not run the same trail twice.

Most of the route is on unpaved surfaces : about 90 percent on dirt with rocks and roots : and is largely shaded by tree cover. The start area is at the Thomas Paine Cottage in New Rochelle and the finish is at New Rochelle High School, directly across the street from the start. The event is hosted by the NewRo Runners club and is part of the Trail Mix Series, a set of seven trail races in Westchester County, NY and Fairfield County, CT.

Trails used in the race are often away from public view and support local wildlife; observed species include deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, and bald eagles. Historical race results and course records are published for prior years. Additional race information, event listings, and participant resources are maintained by the organizers. Visit the organization's website for the most recent information.

Race information

Half Marathon
Paine to Pain Trail Half-Marathon
Visit the organization's website for the most recent information.
Trail runs nearby

A trail race at South Mountain Reservation on February 21, 2026 offering 50M, 50K, 20M and 10M on an approximately 10 mile loop with aid stations, electronic timing, event SWAG and top-three awards.

A 3 x 2 mile cross country relay at Sunken Meadow State Park in Kings Park, NY, marking the 47th running of the event. The program includes a youth division, a costume contest with prizes, post race refreshments and multiple age categories.

A trail running event at South Mountain Reservation on March 7, 2026 offering five distances across three repeatable loops. The course features mixed surfaces, substantial elevation gain, handcrafted wood medals, and fundraising options for..

Looped hill races at Sunken Meadow State Park where the most distance in a three hour loop crowns the King and Queen, and a separate one hour event crowns the Prince and Princess.