Rhode Island has become a popular destination for celebrities looking for a retreat, with big-name part-time residents including Judge Judy Scheindlin, Jay Leno, Christopher Walken, James Woods, and Taylor Swift. Swift’s $17.75 million Watch Hill mansion has garnered attention, inspiring her song “The Last Great American Dynasty” that narrates the history of her property, known as Holiday House. The Ocean State getaway is a favorite of Swift’s, where she hosts famous friends.
Swift’s famous neighbors in Westerly include Conan O’Brien’s parents and sports media personality Colin Cowherd. Locals are protective of Swift’s privacy, but appraisals of her security measures have sparked some controversy, particularly in impeding access to the popular seawall. Swift has hosted Fourth of July parties at her home, welcoming famous friends like Blake Lively, Ruby Rose, and Selena Gomez.
Watch Hill, a village in Westerly, features small shops and eateries alongside beautiful scenery and landmarks such as Watch Hill Light and Flying Horses Carousel. The village has been a draw for famous visitors for decades, with celebrities like Billy Joel, Oprah Winfrey, and Drew Barrymore enjoying visits. Westerly is conveniently located within a two-hour drive from Boston and three hours from New York City.
Celebrities have been drawn to Watch Hill’s charm for years, with events like the wedding of Olivia Culpo and Christian McCaffrey taking place at the luxurious Ocean House. The area’s history, natural beauty, and proximity to major cities make it an appealing destination for those seeking a quiet retreat with a touch of glamour.
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