Paine to Pain Half Marathon Trail Race

Paine to Pain Half Marathon Trail Race “These are the trails that try men's soles.” (Sort of.) - Thomas Paine, The American Crisis, Dec. 23, 1776 WHERE: New Rochelle (at North Ave.

Paine to Pain Trail Half-Marathon, hosted by NewRo Runners, is a giant single loop that winds its way through the woods and trails of five different parks in lower Westchester County. You never run the same trail twice and will spend 90% of your time on dirt (and rocks and roots) in the shade of the woods. Many of the trails are completely hidden from public view and host a wide variety of wildlife including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, bald eagles, and other critters. and Broadview Ave.), just 4 train stops north of Midtown Manhattan

Start: Thomas Paine Cottage, New Rochelle (click here for Google map)

End: New Rochelle High School

WHEN: Sunday, October 12, 2025, 9 a.m. (registration opens Tuesday, April 22)

Paine to Pain is part of the Trail Mix Series, which showcases seven great trail races in New York’s Westchester County and Connecticut’s Fairfield County.

04/19/2025

WHERE: New Rochelle

WHEN: Sunday, October 12, 2025, 9 a.m.

Start: Thomas Paine Cottage, New Rochelle

End: New Rochelle High School

REGISTRATION: Opens Tuesday, April 22

Address

New Rochelle, NY

Website

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