New York State Route 416 (NY 416) is a state highway located entirely within the towns of Hamptonburgh and Montgomery in Orange County, New York, in the United States. It extends for 4.24 miles (6.82 km) in a north–south direction from an intersection with NY 207 in Hamptonburgh to a junction with NY 211 in Montgomery. It does not intersect any other state routes besides those at its termini, nor pass through any settlements. NY 416 is a two-lane highway for its entire length, and mainly serves to allow traffic from the northwestern corner of the county to get to Goshen, the county seat, more easily. Despite its minimal length, the route passes a number of places of interest and is a quite scenic country road. The route was assigned as part of the 1930 renumbering of state highways in New York.

Hamptonburgh is a town located in the north central part of Orange County, New York, United States. The population was 5,489 at the 2020 census. The municipal offices are at the hamlet of Campbell Hall.