Logo

Paine to Pain Trail Half Marathon

New Rochelle, United States • 12 Oct 2025

The Paine to Pain Trail Half-Marathon is an annual trail running event held in Westchester County, New York, typically in October. It features a challenging course that winds through the woods and trails of five different parks, with most of the race on dirt, rocks, and roots, offering a scenic and immersive experience in nature. The race starts at the Thomas Paine Cottage in New Rochelle and ends at the high school in the same city. Known for its scenic trails and wildlife, it attracts trail runners seeking a unique and rugged half-marathon. The event is part of the Trail Mix Series and emphasizes community, outdoor adventure, and trail running excellence. Visit the organization's website for the most recent information.

United States New York New Rochelle

Race information

Website
13 mi
Half Marathon
Visit the organization's website for the most recent information.
Trail runs nearby

Nassau Suffolk Trail Marathon

Farmingdale - 21 mi from New Rochelle

The Nassau Suffolk Trail Marathon & 15 Miler is a premier running event taking place in Farmingdale, NY, on May 18, 2025. This event features two main races: a full marathon and a 15-mile trail run, both set in the scenic Bethpage State Park. Participants will enjoy a well-marked course that include..

Spring Run The Farm - Katonah, NY

Katonah - 24 mi from New Rochelle

The Spring Run The Farm event, scheduled for May 18, 2025, in Katonah, NY, features a 5-mile trail race and two kids' races. The main event is open to participants aged 6 and older, while the kids' races cater to ages 7-12 and 6 and under. The race takes place at Muscoot Farm, showcasing the area's..

Forest Park Runners Classic Trail Race

Queens County - 12 mi from New Rochelle

The Forest Park Runners Classic 4 Mile Road and Trail Race is set to take place on May 25, 2025, at Victory Field Track in Woodhaven, NY. This event features a scenic 4-mile out-and-back course through the beautiful trails and roads of Forest Park. Participants can expect custom technical T-shirts a..

Sri Chinmoy 24-Hour

Valley Cottage - 16 mi from New Rochelle

The Sri Chinmoy 24-Hour, 12-Hour, and Midnight Marathon is a scenic ultramarathon event held at Rockland Lake State Park near New York City. Participants can choose between a 24-hour race, a 12-hour race, or a midnight marathon, all taking place on a flat, fast 2.95-mile paved loop around the lake...

Pinky’s Rock n Rolla

Richmond Hill - 15 mi from New Rochelle

Pinky’s Rock n Rolla is a unique trail running event taking place in Richmond Hill, NY. This four-mile race offers participants the chance to experience actual trail running through the scenic Forest Park, featuring natural terrain shaped by glaciation. The event is designed for both newcomers and s..

The Squatchy Surprise

West Orange - 25 mi from New Rochelle

The Squatchy Surprise is a unique trail running event held at South Mountain Reservation in West Orange, New Jersey. Scheduled for July 26, 2025, it offers 12-hour, 6-hour, and 3-hour race options. The event features four distinct trail loops, with participants drawing colored golf balls to determin..