Living in Port Chester: Things to Do and See in Port Chester, Westchester County, New YorkPort Chester is a 2.4-mile coastal village within the town of Rye in Westchester County, New York. Nicknamed the “Gateway to New England,” Port Chester borders the state of Connecticut; just east is Greenwich, one of the most affluent cities in America. Port Chester evolved from an industrial town to a major seaport in the 19th century due to its location along the Byram River. Today, it’s an attractive suburban village with a scenic waterfront; parks and recreation areas; a historic downtown with a theater, galleries, fine shops, and excellent restaurants; and a train station with direct service to Midtown Manhattan. Port Chester has six parks, waterfront plazas, and a pedestrian-friendly downtown, making its “Walk Score” 78/100—higher than Washington, DC, Chicago, and Seattle.