Watch Hill


Taylor Swift’s squad famously descends on this part of Westerly for the Fourth of July, but any day is perfect for a visit.



Shops along Bay Street and Fort Road offer beautifully curated summer shopping, from the colorful – and covetable – summer prints at Lilly Pulitzer (31 Bay St.) to nautical-inspired bags made from recycled sails at Sea Bags (101 Bay St.). Discover an unmatched selection of women’s swimsuits at JC’s of Watch Hill (62 Bay St.), men and women’s apparel in unlimited prints and colors at Three Islands (99 Bay St.), and both the latest trends and classic fashion at Rochelle’s Boutique (117 Bay St.). Be awed by the large-scale, colorful paintings on display at Jeanette Vertentes Studio (147 Bay St.). 



St. Clair Annex (141 Bay St.) is Watch Hill’s iconic ice cream parlor and clam shack. Olympia Tea Room (74 Bay St.), even at over 100 years old, this spot continues to put a fresh spin on classic New England fare. For sweets, head to The Candy Box (14 Fort Rd.), a quintessential coastal candy shop, and Downtown Westerly’s gelato spot has its seasonal Pompelmo by the Sea (12 Fort Rd.) that’s perfect on a warm summer day. Feeling luxurious? While staying at Ocean House (1 Bluff Ave.) can be pricey, the hotel is visitor friendly, especially the expansive Verandah Raw Bar that’s perfect for people-watching over cocktails. Restaurants range from a more casual gastropub and patio snacks to a fine dining experience and champagne garden.  



East Beach is the little strip of white sand between Ocean House (1 Bluff Ave.) and Taylor Swift’s mansion. Parking can be a challenge, but it’s worth it. Watch Hill’s Napatree Point (Ford Rd.) is a popular spot for beachgoers, and it’s also a nature preserve where endangered piping plovers nest, so it’s 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 small downtown area of Watch Hill is on the National Register of Historic Places. The Flying Horse Carousel (151 Bay St.) is the oldest continuously operating carousel in the country, and The Watch Hill Lighthouse (14 Lighthouse Rd.), a 15-minute walk from downtown Westerly, dates back to 1856, and its museum is typically open to the public in July and August.


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