Wingdale is a hamlet and census-designated place (CDP) in the town of Dover in Dutchess County, New York, United States.

The hamlet of Wingdale is in the northern part of the CDP, while the Evangelical Center is in the south, on the grounds of the former Harlem Valley State Hospital, and scattered housing occupies the hills in the eastern part of the CDP.

New York State Route 22 runs through the CDP, passing east of Wingdale hamlet.

The highway leads north 7 miles (11 km) to Dover Plains and south the same distance to Pawling.

State Route 55 runs concurrently with NY 22 to the south, but turns east at Wingdale and leads 6 miles (10 km) to Gaylordsville, Connecticut.