Watch Hill is an affluent coastal neighborhood and census-designated place in the town of Westerly, Rhode Island. The population was 154 at the 2010 census. It sits at the most-southwestern point in Rhode Island. It came to prominence in the late 19th and early 20th century as an exclusive summer resort, with wealthy families building sprawling Vict…Watch Hill is an affluent coastal neighborhood and census-designated place in the town of Westerly, Rhode Island. The population was 154 at the 2010 census. It sits at the most-southwestern point in Rhode Island. It came to prominence in the late 19th and early 20th century as an exclusive summer resort, with wealthy families building sprawling Victorian-style "cottages" along the peninsula. Watch Hill is characterized by The New York Times as a community "with a strong sense of privacy and of discreetly used wealth," in contrast with "the overpowering castles of the very rich" in nearby Newport.