Paine to Pain is a giant single loop that winds its way through the woods and trails of five different lower Westchester parks. 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, hawks, owls, heron, wild turkey, rabbit and other critters.
Where: Start/End in New Rochelle, just 4 train stops north of midtown Manhattan.
Start at Thomas Paine Cottage, New Rochelle, New York. (map). End at New Rochelle High School. (Both at the intersection of North Ave. and Broadview Ave.)
Parking: If you are unfamiliar with the area