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When rumors surfaced that Taylor Swift celebrated her bachelorette party in Watch Hill, Rhode Island, last month, I wasn’t the least bit surprised. I’ve been visiting this tiny seaside village in the town of Westerly for the past five summers, and while Swift’s oceanfront mansion has made it one of New England’s most recognizable celebrity hideaways, Watch Hill has long been worth visiting in its own right.
Perched on Rhode Island’s southwestern coast, Watch Hill is the kind of place where mornings begin with coffee and a walk on the beach, afternoons are spent browsing boutiques or lounging by the water, and evenings revolve around fresh seafood, cocktails and sunsets over Block Island Sound. The village is small enough to explore entirely on foot, yet packed with enough great restaurants, beaches and shops to easily fill a long weekend.
Whether you’re a Swiftie curious about her seaside neighborhood or simply planning an elevated girls’ getaway, here’s exactly how I’d spend a weekend in Watch Hill.
What to do
Start your morning with a walk out to Napatree Point, a protected stretch of beach and dunes at the southernmost and westernmost point of mainland Rhode Island. Its 86 acres feature sweeping views of Block Island Sound, plenty of birdlife and enough open shoreline that it rarely feels crowded, even at the height of summer.
Next, wander through Watch Hill’s historic village center, browsing the boutiques along Bay Street before taking a ride on the Flying Horse Carousel, the oldest continuously operating carousel in the country. It’s a local tradition and worth doing at least once. (I’m looking forward to taking my twin toddlers on it next month!)
In the afternoon, stretch out on the three-mile expanse of East Beach, which runs from the Watch Hill Lighthouse to Ocean House; alternatively, get out on the water with a voyage aboard the wooden sailboat Trim Again. The beauty of Watch Hill is that there’s no need to rush—everything is close enough to explore on foot, and the best days are often the ones without a set itinerary.
Where to eat
Kick off your day at Nana’s Bakery, an all-day café that’s worth visiting whether you’re stopping in for breakfast, lunch, dinner or cocktails. If you can snag a table in the morning, don’t skip the sourdoughnut French toast, made with the bakery’s signature sourdough doughnuts. Pair it with a glass of Rhode Island coffee milk—the state’s official drink—for the full local experience. If breakfast is packed (and it usually is on summer weekends), come back later for lunch, dinner or drinks.
There’s also the Cooked Goose, a longtime breakfast-and-lunch spot that’s been a Westerly favorite for more than 20 years. The menu leans classics—think hearty breakfasts, scratch-made pastries and excellent coffee.
For lunch, head to Ten Sandwiches, where the menu lives up to its name with just 10 thoughtfully crafted sandwiches, plus a handful of salads and smoothies perfect for a beach picnic. If you’re sticking around into the evening, the menu expands to include light bites, pizzas and cocktails.
If you’re heading to the beach, make a stop at St. Clair Annex to pick up one of its signature grinders (Rhode Island–speak for a sub), a lobster roll or a BLT. Then, swing back later for dessert. The longtime local favorite is known for its homemade ice cream, with dozens of flavors ranging from classics like black raspberry chocolate chip to seasonal creations like s’mores and peach cobbler. If you really want to indulge, order a hot fudge sundae or a banana split and thank me later.
For dinner, head to Olympia Tea Room, a Watch Hill institution for more than 100 years that’s evolved well beyond its name. Grab a table on the lively sidewalk patio or inside the cozy dining room, then order local seafood, a grilled pizza or something from the restaurant’s award-winning wine list featuring more than 100 selections. If you’re visiting Thursday through Sunday, it’s also a great lunch spot.
If you’re celebrating—or simply looking for an excuse to splurge—make a reservation at Coast at the swanky Ocean House resort, which also happens to sit next door to Ms. Swift’s mega-mansion. The multicourse tasting menus change with the seasons and feature inventive dishes like lobster poached in white chocolate (yes, really) or duck with mole. For something more casual, I like settling in at The Bistro for classic New England fare or dining alfresco at the covered Verandah Raw Bar, where lobster rolls, oysters and cocktails come with sweeping views of the Atlantic.
Where to sip cocktails
When the weather is nice, my first choice is the aforementioned Verandah Raw Bar at Ocean House. There’s nothing better than lingering over oysters, a crisp glass of wine or a summer cocktail while looking out over Block Island Sound.
For something more intimate, River Bar in downtown Westerly stands out for its inventive cocktails and cozy atmosphere, making it a great spot before or after dinner. The weekday happy hour is also one of the best in town, with bites from $4, plus $4 draft beers, $10 wines and a rotating $10 cocktail of the day. Evie’s Cocktails & Comforts never takes itself too seriously, and that’s part of the appeal. The creative cocktail list is packed with cheeky names inspired by movies and pop culture—from “I Carried a Watermelon” and “Why Is the Rum Always Gone?” to “She Doesn’t Even Go Here.”
Perks & Corks offers the best of both worlds, as one part coffeehouse, one part bar. Stop in for an afternoon coffee or linger into the evening over one of its 55-plus signature martinis—including an espresso, chai or the unforgettable extra dirty gorgonzola—along with wine, beer and classic cocktails.
Need a change of scenery? Make the short drive to Westerly’s Misquamicut Beach, where The Andrea Seaside Restaurant & Beach Bar, Paddy’s Beach Club and Windjammer Surf Bar serve frozen drinks and fresh seafood with a side of live music and unbeatable ocean views.
Where to stay
If you’re splurging, Ocean House is the obvious choice. The iconic yellow Victorian hotel sits directly above the beach with beautifully appointed rooms, multiple restaurants, a Forbes Five-Star spa and impeccable service. As previously mentioned, it also happens to sit just steps from Taylor Swift’s famed Watch Hill estate, making you about as close as you can get to calling the pop star your neighbor for the weekend.
Traveling with a group? Consider Watch Hill Inn, Ocean House’s sister property. Its spacious apartment-style suites—with full kitchens and separate living areas—offer a more residential feel while putting you just a short walk from the beach and the shops and restaurants lining Bay Street. Best of all, guests also enjoy access to many of Ocean House’s amenities, including its private beach, pools, spa, fitness center, and complimentary resort shuttle.
For a quieter escape, head just 10 minutes away to neighboring areas of Westerly. Weekapaug Inn—another Ocean House sister property—offers a luxurious retreat overlooking Quonochontaug Pond, complete with beautifully appointed rooms, a robust summer activities calendar (think sailing, birding, stargazing, movie nights and more), beach access, an excellent waterfront restaurant and wellness programming like yoga, meditation and sound healing. Also in Westerly, the charming Margin Street Inn looks like it was plucked straight from a storybook with its Victorian architecture, landscaped grounds and cheery rooms.
If you only do one thing…
Beeline to the Verandah Raw Bar at Ocean House just before sunset. My husband and I always order Aperol spritzes and a dozen freshly shucked oysters before wandering the property’s beautifully landscaped paths down to the beach to watch the sun dip below Block Island Sound. After five summers in Watch Hill, it’s still my favorite ritual—and the first reservation I make every time we plan a trip.