Paine to Pain Trail Half Marathon

Prepare for an unforgettable journey at the Paine to Pain Trail Half Marathon, taking place on Sunday, October 11, 2026, in New Rochelle, NY. This 13.1-mile single-loop course is celebrated as one of the premier trail half marathons in the region, offering runners a challenging yet incredibly scenic experience. Approximately 90% of the route traverses dirt, rocks, and roots through five diverse lower Westchester parks, ensuring you never run the same trail twice and are largely shaded by the dense woods. Runners consistently praise the well-marked course, which is teeming with local wildlife such as deer, fox, and various birds, making it a true escape into nature.

The Paine to Pain Half Marathon is renowned for its rugged terrain, particularly in the more technically demanding first half, which includes rocky sections and notable elevation changes, accumulating over 1,000 feet of gain across the course. Expect to slow your pace by about a minute per mile compared to road races. Aid stations are strategically placed around miles 4, 7, and 11, with additional volunteers offering encouragement along the way. The race kicks off with a unique atmosphere at the historic Thomas Paine Cottage, where participants can expect a jovial start, complete with cheerleaders and even a revolutionary band and musket. Finishers will cross the line at New Rochelle High School, just across from the start.

Typical race day conditions in mid-October offer ideal running weather, with historical highs around 69°F and lows around 56°F, and a low 13% chance of precipitation, providing a comfortable environment to tackle the trails. This event, organized by NewRo Runners and part of the esteemed Trail Mix Series, offers a truly unique blend of natural beauty, historical significance, and a supportive community atmosphere, making it a must-do for both seasoned trail runners and those looking for an engaging new challenge.