A Weekend Traveler’s Guide to Watch Hill, Rhode Island

An aerial view of the sprawling and scenic Ocean House Hotel. / Photo courtesy of Ocean House, Rhode Island

While other Gilded Age summer colonies have ossified into museum pieces, Watch Hill, Rhode Island, retains all the magnificence of its original heyday, along with a low-key attitude and tremendous charm. A veritable Brigadoon of handsome shingle-style mansions, it’s successfully escaped Disney-fication and remains almost absurdly picturesque. No wonder it’s captivated everyone from Albert Einstein to Groucho Marx, along with the well-heeled likes of Henry Ford and Andrew Mellon. Other than Taylor Swift, though—who famously owns a rambling white heap on Bluff Avenue that once belonged to Standard Oil heiress Rebekah Harkness—the money is resolutely old and quiet. New York Knickerbocker families and the descendants of Midwestern industrialists sip gin and tonics and don tennis whites to play generational grudge matches at the Misquamicut Club or slip into Topsiders to sail out of the Watch Hill Yacht Club.

Even without entrée to these rarefied spaces, a casual summer visitor can enjoy all the best Watch Hill has to offer, from its magnificent beaches to the local ice cream shop, which has been tickling sweet tooths since 1887.

A ride on the Flying Horse Carousel. / Photo via Creative Commons/Robellin

Play

A trip to Watch Hill is a bit like stepping into a Slim Aarons photograph, offering a refined taste of the good life from a more civilized age. There isn’t a summer diversion you won’t find in the area, from volleyball on the beach to surfcasting and birdwatching at Napatree Point Conservation Area. Local landmarks include the Watch Hill Lighthouse, the Flying Horse Carousel (which claims to be the oldest continuously operating carousel in the country), and the stately grand dame of Watch Hill, Ocean House hotel. There, you can rub elbows with the local gentry at the Verandah over cocktails and a signature seafood tower or take a croquet lesson on the perfectly maintained lawn from national champion and in-house pro Stephen Morgan.

The lobster roll from the Restaurant at Weekapaug Inn. / Photo courtesy of Weekapaug Inn, Rhode Island

Eat

First things first: No visit to Watch Hill is complete without a stop at the St. Clair Annex, a family-owned ice cream and sandwich shop operated by the Nicholas family for more than 135 years. In addition to the delicious small-batch ice cream, they make a mean grinder (our favorite is the Italian). The Olympia Tea Room, which dates to 1916, doesn’t accept reservations, but dishes like linguini with roasted clams and Portuguese baked haddock make the wait for one of the antique mahogany booths worthwhile. For fine dining, head over to the nearby Weekapaug Inn, the Relais & Châteaux sibling of Ocean House, for dinner at the Restaurant (don’t miss the Stonington scallops and Crescent Farm duck duo). And finally, all of the dining options right at Ocean House—from the Bistro, with its classic burger and crab cakes, to the award-winning Coast, with its five-course degustation menu of elevated seasonal cuisine—are tiptop.

Shop

Pretty much the entirety of Watch Hill’s retail district is located on Bay Street and ranges from little souvenir shops to chic boutiques. The trendy women’s clothing boutique Rochelle’s has done so well that it’s expanded to five more locations; the quirky and charming Lolo, meanwhile, carries beach and pet toys in addition to scented candles, cocktail napkins, puzzles, and other excellent hostess gifts. And WH2O, operated by husband-and-wife team Eric and Georgia Jones, carries a fun selection of items, including Brackish bow ties, nautical-themed tea towels and napkin rings, and jewelry for both men and women.

Serene poolside seating at Ocean House. / Photo courtesy of Ocean House, Rhode Island

Stay

With its extensive gardens and swanky beach club, the iconic yellow-and-white Ocean House boasts, among other things, the world’s largest collection of work by the French illustrator Ludwig Bemelmans (creator of Madeline). Kids will be enchanted by the hotel’s self-guided Mortimer Mouse Scavenger Hunt, while couples can canoodle in one of the 49 spacious rooms that have hosted the likes of Hugh Jackman and offer commanding views of Block Island Sound.

Getting There

Although Watch Hill is as far south as you can go in Rhode Island (it’s literally on the Connecticut border), there are no bridges to cross or ferries to take, making it a hassle-free two-hour drive on I-95.

Napatree Point Conservation Area offers 86 acres of prime bird-watching. / Photo by Michael St. Jean/Getty Images

First published in the print edition of the July 2023 issue with the headline “Watch Hill, Rhode Island.”