Where to Stay:
With its bright yellow exterior, the crown jewel of Watch Hill is the opulent Ocean House. Originally built in 1868, this iconic property got a second wind in 2010 with a floor-to-ceiling rebuild (another refresh took place just before the 2017 summer season). In addition to pristine white beaches, the property boasts an ample grass lawn perfect for croquet. But for another sort of outdoor leisure, enter the Veuve Clicquot-branded “Secret Garden” cocktail patio, where you can enjoy a variety of Veuve vintages and Champagne cocktails with your beach views.
What to See:
The town hasn’t changed much since its early days as a charming vacation town for well-to-do families, retaining charming landmarks like the Flying Horse Carousel. Built in 1867, it is thought to be the oldest continuously operating carousel in the U.S. Just steps away is Watch Hill Beach, a family-friendly stretch offering equipment and cabana rentals. And whether you’re a birdwatcher or sucker for a gorgeous sunset, Napatree Point conservation area, just down from Watch Hill Beach, offers a visual feast.
Where to Shop:
At the center of life in Watch Hill is Bay Street, home to a multitude of apparel and home décor shops, each one seemingly more adorable than the last. There you will find everything from elevated surfer vibes at Huxter to unusual gemstones paired with modest elegant design at Christina Stankard. And it wouldn’t be an old money outpost without a Lilly Pulitzer, located just off Bay Street, which recently collaborated with the Watch Hill Inn on a custom suite.
Where to Eat:
Rise and shine with an organic nitro iced coffee on tap at the newly renovated 10 Sandwiches, then load up lobster rolls and homemade blueberry ice cream at the classic St. Clair Annex, opened in 1887. For dinner, there’s no better spot in town than the Olympia Tea Room. After more than 100 years, Olympia continues to draw crowds with its award-winning wine list, locavore-friendly menu, and seasonal cuisine.