Watch Hill: A Yankee Insider’s Guide

Sponsored by Mark & Graham, a Williams Sonoma brand

Fewer than 200 people call Watch Hill home, but this Victorian village in the town of Westerly, Rhode Island, has outsized allure thanks to its swoosh of beach; classic New England attractions; upscale shopping, sipping, and dining; and luminous sunsets. Find your way to this high peninsula, and you’ll instantly understand why famous Watch Hill homeowners Taylor Swift and Conan O’Brien retreat here on occasion. Watch Hill’s been the choice for vacationers with the means to travel anywhere since the latter half of the 19th century, when steamboats and, later, electric trolleys deposited them here.

While yachts sway in the harbor, kids squeal as Watch Hill’s historic Flying Horse Carousel defies the bounds of typical up-and-down merry-go-rounds. There’s a breezy elegance that speaks of simpler times, yet everywhere you look, there’s a scene that’ll make you glad the phone in your beach bag can capture images … and memories.

Speaking of beach bags, Mark & Graham’s classic, chic summer line seems tailor-made for Watch Hill escapes. As you design your trip with our Yankee editors’ insider advice on where to stay, eat, and play in Watch Hill, picture yourself toting everything you need for beach days and starry nights in style.

Where to Stay

GRAND HOTEL | Ocean House

There will always be echoes of 1868 at this lemon drop–colored Victorian grand dame overlooking the tumbling sea. But since the historic Watch Hill hotel was rebuilt in 2010, it’s achieved a level of modern luxury unequaled in New England. Yes, it costs a pretty penny to stay, particularly during the summer high season, when beach cabanas, yachting adventures, and rounds of croquet are on offer. But you don’t need a room key to nab an open-air table on the verandah for drinks and local oysters. Just toss on a swishy sundress or crisp slacks, and go live the life.

BUDGET-FRIENDLY INN | Watch Hill Harbour House Inn

When you have celebrity-getaway tastes but not the champagne budget to go with them, you’ll find this under-the-radar, 12-room inn an affordable place to lie your head. And it’s mere steps to Watch Hill Beach. OK, it’s a six-minute walk, and Taylor Swift could beat you there by three minutes. But you can’t put a price tag on the blissful anonymity you’ll enjoy as you flip-flop your way to the shore.

LUXURY B&B | Margin Street Inn

The simplicity-loving Quakers who built the 19th-century Greek Revival and Colonial Revival mansions that make up this luxurious inn might raise an eyebrow if they could see what their former homes have become. But modern guests revel in the beautifully styled common spaces, the spacious suites outfitted with fine linens, the morning reveal of artist and innkeeper Sarah Cooper’s ever-changing frittatas, and the landscape adorned with heritage trees and historic outbuildings. Watch Hill is a pleasant 5-mile drive south.

FAMILY-FRIENDLY LODGING | The Hotel Maria

Just three miles east of Watch Hill in the Misquamicut area of Westerly, this cheery boutique lodging property is directly across the street from prime sand. The Bellone family has deep hospitality roots in this corner of Rhode Island, and late matriarch Maria would have adored her namesake hotel and its private stretch of beach. You’ll adore it too: Rooms are cottage-chic and spacious, a complimentary guest pantry is available 24/7, cute custom bikes are yours for the borrowing, and your beach bag and towels are waiting. 

WATERFRONT INN | Watch Hill Inn

With all the amenities of its acclaimed sister property, Ocean House, just a short walk away, this lavish, all-suite property gives families and small groups a luxurious option for extended stays. With ultra-modern kitchens, waterview terraces, fireplaces, and designer touches, these 600- to 4,000-square-foot accommodations feel like dream homes.

What to Bring

CLASSIC NAVY LUGGAGE | Terminal 1 Luggage Set

Your Watch Hill vacation begins the moment you toss a swimsuit into one of Mark & Graham’s classic navy suitcases. This expandable carry-on and checked luggage two-piece set covers all of your bases when coastal escapes beckon. Leather detailing and custom monogramming set this lightweight yet rugged luggage apart.

WATERPROOF TOTE | Raffia Bamboo Tote

Whether you’re living the boat life or chilling on the beach in Watch Hill, Mark & Graham will help you protect your shades, sunhat, and scintillating beach read from splashy mishaps. We’re fans of this waterproof tote with its stylish bamboo double handles and vegan-leather shoulder strap. It’s oversized, which you’ll appreciate when you take a break from lounging waterside to duck into the boutiques along Watch Hill’s Bay Street.

ZIP-TOP TOTE | Mark & Graham X Steele Multi Pocket Tote

Prefer a zip-top tote? This carry-all bag is also waterproof, and thanks to Mark & Graham’s collaboration with enduring New England brand Steele Canvas, it’s the perfect blend of fashion and function.

MAKE-UP CASE | Clear Coated Travel Case

Available in fun patterns (Navy Shell is our pick) in a coastal rainbow of blue and coral shades, you’ll fill this Mark & Graham staple with Watch Hill beauty essentials like sunblock, scrunchies, and waterproof mascara. An embroidered monogram makes it uniquely yours. A wipeable coating inside and out keeps this must-have travel accessory looking fresh as a summer morning.

Where to Eat

DOUGHNUTS | Knead Doughnuts

Lucky for you, Rhode Island’s best doughnuts have migrated out of Providence to a seasonal location in Westerly, and it’s for-“shore” worth the 12-minute drive inland to get your hands on these elevated classics. Look for the varieties made of brioche dough, a recipe of fresh yeast, butter, and real vanilla bean, fermented for 24 hours for maximum flavor. The Jelly is a masterpiece of hand-rolled brioche filled with seasonal jam and tossed in granulated sugar. “Knead” we say more?

BISTRO | Olympia Tea Room

“Famous not fancy” since 1916, this seasonal favorite on the lively main drag in Watch Hill is a sweet place to duck out of the sun for a cocktail and a bite. The wine list will surprise you, as will calamari two ways. Try them both: Calamari is Rhode Island’s official state appetizer. Keep it light with a salad and half-dozen local oysters, or carb load for more boogie boarding with a robust pasta dish.

LUNCH AND ICE CREAM | St. Clair Annex

This family-owned restaurant traces its Watch Hill lineage back to 1887, and it’s an affordable option when you’re feeding a large crew and don’t want to wander far from your sandy spot on Watch Hill Beach. Chase a hearty burger or grinder (that’s Rhode Island lingo for a submarine sandwich) with ice cream, made right here in small batches, as it always has been.

LOCAVORE CUISINE | The Restaurant at Weekapaug Inn

This refined yet casual Relais & Châteaux property set on lovely Quonochontaug Pond is mindful of its sensitive coastal environment in myriad ways. Located about a 15-minute drive east of Watch Hill, it’s worth a visit just to treat your palate to a taste of super-fresh local cuisine. No food ingredient travels more than 155 miles to reach the property’s kitchens, and all scraps are composted and repurposed. The lobster rolls here, served hot or cold, are a worthy splurge.

What to Do

BEACH FUN | Watch Hill Beach

Tucked right behind Watch Hill’s nostalgic carousel, this petite beach is ideal for families. There’s an admission fee, but it’s a small price to pay for soft, clean sand, lifeguards on duty, and views of Watch Hill Lighthouse. Arrive early to have a prayer of finding parking on peak summer days, or consider using a ride service. Once you’ve staked your spot, you’ll be glad you packed travel games from Mark & Graham like this Mini Mahjong Set or Magnetic Backgammon to encourage screen-free play by the shore.

BEACH STROLLS | Napatree Point Conservation Area

Saunter along Block Island Sound, and experience a stretch of beach allowed to revert to its natural state.You’ll be soothed by the waves as you spot the small harbor of Stonington, Connecticut, and the dome of trees atop Fishers Island, New York, in the distance. On the return trip, savor the view of the Victorian houses that cling to the Watch Hill bluffs.

FOR KIDS ONLY | Flying Horse Carousel

Most carousel horses go up and down, but the ones at this beachside merry-go-round in Watch Hill prefer centrifugal force. America’s oldest operating carousel featuring ponies suspended from chains has delighted children (riders must be 12 or younger) since 1883, when it was abandoned here by a traveling carnival. The 20 hand-carved steeds “fly” outward as they accelerate, giving riders a chance to snatch the brass ring for a free ride.

LIGHTHOUSE | Watch Hill Lighthouse

Walk down private Larkin Road in Watch Hill for an up-close view of the village’s granite 1855 lighthouse. There’s a museum with seasonal hours on Tuesday, Wednesday, and Thursday afternoons, where you can learn about the now-obsolete role of lighthouse keepers, about notable shipwrecks, and about the Hurricane of ’38’s devastating impact on Watch Hill.

MOVIES AND MORE | The United Theatre

This 1926 theater in downtown Westerly hasn’t just been recently renovated—it’s been transformed. Three screening rooms, a black-box theater, and other performance and display spaces occupy the restored vaudeville venue as well as the long-shuttered Montgomery Ward department store next door. You can catch a movie, hear a band, attend a lecture, browse an art gallery, or pose in a yoga class.

SHOP | Three Islands

Watch Hill is like a mini Chatham, Massachusetts, for those who love to shop. Within a brief stretch, there’s a candy store, an ice cream parlor, and boutiques including Three Islands. Founded by cousins Justin Goff and Phil Barney, who became smitten with all things Bali while on a surfing trip, the clothing brand’s seasonal flagship is where you can find “a little sunshine for your closet,” made from hand-screened batik.

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