18th Annual

A drawing of a man dressed in colonial attire, with a tricorn hat, curly hair, enclosed within an oval. The illustration uses navy blue, red, and white colors.

Paine to Pain Trail
Half-Marathon!

Westchester County, New York

Sunday, October 11, 2026

2025 Race Highlights

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 fauna.

WHERE: New Rochelle (at North Ave. 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 (across the street from the start)

WHEN: Sunday, October 11, 2026, 9 a.m.

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.