Watch Hill, Rhode Island, a charming coastal town, has long held a special place in the hearts of many, but it gained a new level of fame when Taylor Swift purchased the historic Holiday House in 2013. This sprawling estate has since become synonymous with summer celebrations, hosting numerous celebrity-studded Fourth of July parties, including Blake Lively’s recent 37th birthday bash.
Swift’s connection to the town even inspired her song “The Last Great American Dynasty” from her 2020 album Folklore. The song beautifully portrays the home’s rich history and the colorful personality of its former matriarch, Rebekah Harkness.
Watch Hill, a haven for those seeking a more serene getaway than the Hamptons or Nantucket, is located on the southernmost tip of Rhode Island. This quaint town, a part of the larger Westerly, boasts a collection of beautifully restored historic homes and renowned residents.
Where to Stay
To fully embrace the beauty of Watch Hill, a stay at the Ocean House is an absolute must. This sprawling waterfront Relais & Châteaux property, celebrating its 150th anniversary, provides an unparalleled experience. With endless amenities, including private beach access and a 12,000-square-foot spa, Ocean House is a haven of relaxation and luxury. Their Center of Wine and Culinary Arts offers a delightful escape from the sun with immersive classes held in their wine cellar-inspired school. Guests can also explore the town and surrounding area in style, utilizing the pastel-colored bikes and Mercedes vehicles provided by the hotel.
What to Do
Embark on a rejuvenating hike along the scenic Napatree Point trail. This breathtaking stretch offers breathtaking views while providing an invigorating workout. Open year-round, hikers can enjoy a 2-3 mile journey, depending on their chosen turning point. Birdwatchers will particularly appreciate Napatree Point, as it serves as a wildlife preserve and a resting area for migratory birds.
Step back in time at the Flying Horse Carousel, the oldest working carousel in the country. Built in 1876, this captivating attraction features horses that are not fixed to the ground but instead suspended and swing during operation. Marvel at the hand-carved ponies, leather saddles, and authentic tails and manes while enjoying a refreshing ice cream cone from the nearby St. Clair Annex.
Where to Snack
After your exploration of Napatree Point or a day spent basking in the sun, satisfy your sweet tooth at the charming St. Clair Annex. This family-owned ice cream shop, located in downtown Watch Hill, has been serving customers for over 125 years, sourcing their cream from a local dairy.
Immerse yourself in the history of Watch Hill at the Olympia Tea Room, a 100-year-old restaurant. This delightful establishment offers a simple bistro-style menu, perfectly paired with an extensive wine list and craft cocktails. Secure a sidewalk seat to witness a picture-perfect sunset or relax in an antique booth indoors. Due to its popularity, arrive early, as reservations are not accepted.
Indulge in a glass of Champagne, a quintessential vacation treat, surrounded by boxwood hedges in Ocean House’s Secret Garden. Savor glasses of Veuve Clicquot, including the exquisite Veuve Clicquot Rich Rosé. If hunger strikes, the bar offers pre- or post-dinner bites such as truffle popcorn and an array of gourmet hotdogs.
Before heading to the beach or catching a train, visit the old-school candy shop to stock up on saltwater taffy and homemade fudge.
From Taylor Swift’s summer haven to its idyllic beaches and charming attractions, Watch Hill is a destination that promises an unforgettable experience. Whether you’re seeking relaxation, adventure, or simply a taste of celebrity lifestyle, Watch Hill has something to offer everyone.
