Watch Hill

Taylor Swift’s squad descends on this part of Westerly every July 4 weekend, but any day is perfect for a visit.

Cruising the Strip
The small downtown area of Watch Hill is on the National Register of Historic Places. The Flying Horse Carousel at the end of Bay Street is the oldest continuously operating carousel in the country. Shops along Bay Street and Fort Road offer beautifully curated summer shopping, from the sundresses at Christina LTD to nautical home decor at Highpoint Home. St. Clair Annex is Watch Hill’s iconic ice cream parlor and clam shack, but if you’re in the mood for a bigger meal, Olympia Tea Room has been a full-service restaurant for over 100 years. 

The Beauty of Nature

East Beach is the little strip of clear white sand between Ocean House and Taylor Swift’s house. Parking can be a challenge, but it’s worth it. Watch Hill’s Napatree Point is a popular spot for beachgoers, but it’s also a nature preserve where endangered piping plovers nest, so Napatree is a popular bird-watching spot as well. Sandy Point was once attached to Napatree, but hurricane erosion separated the two. The 35-acre island also has a public beach and is a nature preserve. The Watch Hill Lighthouse, a 15-minute walk from town, dates back to 1856 and has a museum open to the public in July and August.

A Day of Luxury
While staying at Ocean House can cost up to $10,000 a night, the hotel is visitor-friendly, especially the on-site spa and expansive Verandah patio bar that’s perfect for cocktailing and people watching. Restaurants range from a more casual gastropub to a fine dining experience, with patio snacks and a new champagne garden. Thursday, Friday and Saturday nights in the summer, the Ocean House hosts open-to-the-public lobster boils on their private beach.