The Village of Pawling is a community in Dutchess County , New York , United States . State Route 22 runs through every town on the East side of Dutchess County , and runs parallel the Business District of Pawling . Metro-North Railroad has two rail commuter rail stations in Pawling , with service to New York City via the Harlem Line , with the Pawling in the town center , and the Appalachian Trail 2 miles north of the village of Pawling .