Vogue’s September cover star Taylor Swift has four homes. Like your average pop star, she has spots in New York and Los Angeles. Then there’s Nashville, where she started her career in country music. And the quartet is rounded out by an estate in...Rhode Island. While this final place might not the most predictable, a visit to the town of Watch Hill makes it easy to see why Swift spends idyllic summer days—and festive Fourth of July parties—in this part of the country. Less crowded than the Hamptons, and easier to reach than Nantucket, Watch Hill is located on the southernmost tip of the state, part of the larger town of Westerly that is known for its massive and restored historic homes and notable residents. It’s a small place, so hard to miss the major attractions, but here’s a guide to planning an idyllic stay.
Where to Stay
Ocean House You can't truly capture the beauty of Watch Hill without mentioning this sprawling estate. Ocean House is a waterfront Relais & Chateaux property celebrating the 150th anniversary of its original build. Amenities are seemingly endless and include access to the private beach and a 12,000 square foot spa. Their Center of Wine and Culinary Arts offers the perfect escape from the sun with classes in their wine cellar-inspired school. Expand your wine knowledge during a wine-tasting with Erin Swain, one of the only female sommeliers on the East Coast. Guests also have access to pastel colored bikes and Mercedes vehicles to explore the town and surrounding area in style.
What to Do
Napatree Point A hike on this stretch combines exercise and unforgettable views. Open year round, hikers can expect to cover two to three miles dependent on the turning point. Birdwatchers are in for an added treat: Napatree Point serves as a wildlife preserve and is a resting area for migratory birds.
Flying Horse Carousel Although adults won't be able to ride on the oldest working carousel in the country, Flying Horse Carousel is still worth a visit. Built in 1876, the horses are not attached to the ground, but are suspended and swing while in motion. Admire the hand carved ponies, leather saddles, and real tails and manes while enjoying an ice cream cone from St. Clair Annex.
Where to Snack
St. Clair Annex When your sweet tooth hits after walking Napatree Point or a long day of bronzing, this ice cream shop will satisfy. The family owned eatery, located in downtown Watch Hill, has served customers for over 125 years and sources their cream from a local dairy.
Olympia Tea Room History is at the forefront of Watch Hill, especially in this 100-year-old restaurant. Olympia Tea Room serves a simple, bistro-style menu to be paired with an extensive wine list and craft cocktails. Snag a sidewalk seat to watch a picture perfect sunset, or lounge in an antique booth indoors. Word to the wise: arrive early, as they don’t take reservations.
Secret Garden A glass of Champagne on vacation is practically a requirement. Sit among boxwood hedges in Ocean House’s Secret Garden and sip glasses of Veuve Clicquot, including Veuve Clicquot Rich Rosé. Should you get hungry, the bar is stocked with pre- or post-dinner bites such as truffle popcorn and an array of gourmet hotdogs.
The Candy Box Schedule a stop at this old-school candy shop to stock up on saltwater taffy and homemade fudge before you head to the beach or off to the train station.