Watch Hill

These days it’s famous because pop star Taylor Swift has a house on the beach here, but Watch Hill, located on a scenic peninsula in the town of Westerly, has been an exclusive summer resort for over a century.

Despite its past and present affluence, there’s plenty for regular people to appreciate about this waterfront village. Watch Hill Beach is home to the Flying Horse Carousel, sometimes called the oldest carousel in the country, Bay Street is lined with shops and restaurants, and the Watch Hill Lighthouse is a short walk from town. For history lovers, there’s a small but striking statue of Ninigret, the Niantic Sachem who ruled this place when the English arrived in the 1600s.