“Turn right at Taylor Swift’s house, make the first left, and follow the road brimming with roses, hydrangea, and cedar-shake ‘’cottages,’ as we like to call them here. You can’t miss it.”

I have just asked for walking directions to Rhode Island’s famous Watch Hill Lighthouse and can’t help but smile at the presumptuous directions — as if everyone knows the locale of the pop star’s white, oceanfront mansion on the bluff. I do, of course. I spotted it immediately upon checking into my room at the iconic yellow-and-white Ocean House, one of the last remaining grand seaside hotels (originally built 1868). Set on 13 acres, the hotel borders Swift’s property; the window of my suite directly overlooks her airy sea house and shares the same blue Atlantic Ocean view. 

Serendipity has once again brought me into the singer’s orbit. In an era where unlikely “Swifties” — from corporate executives to dads accompanying ‘tween daughters to senior citizens and high-profile celebrities — are navigating the globe, flying from city to city and country to country to attend the pop star’s sold-out Eras concerts, I have unceremoniously — and unknowingly — landed in her shadow. My first brush came in the Hallmark movie-channel town of Sidney, set on British Columbia’s Victoria Island, where I visited Victoria Distillers, maker of Empress 1908 Indigo Gin. I had no idea at the time of the cult-like following surrounding the indigo blue-hued gin — created in partnership with the Fairmont Empress hotel and which changes to bright lavender, soft pink, or fuchsia depending on the mixer. But I learned quickly that Lavender Haze Lemonade (made with Empress 1908 Indigo Gin) was created in celebration of Swift’s Lavender Haze song and served as the tour’s signature cocktail.

Now, in the stunning historic sea town of Westerly (and tony Watch Hill neighborhood), I’m once again in the super star’s stratosphere. But as I quickly learn, there’s more to this laidback seaside enclave than Swift’s bluff-top “Holiday House” (once owned by Standard Oil heiress Rebekah Harkness). Just a 1.5-hour drive from Boston and 2.5 hours from New York City, Westerly — lesser known than Newport (Rhode Island), Cape Cod, and Nantucket (Massachusetts) — is arguably New England’s best-kept secret.

The Intrigue  

rooftop terrace, ocean house, Rhode Island
Courtesy, Ocean House

“The beaches are fabulous; the [13-mile] coastline from Watch Hill to Charlestown (with 14 beaches), the best in New England,” says Joe Witherell, concierge extraordinaire at Ocean House, as he ceremoniously hands me a “Miss Clavel,” the hotel’s signature welcome drink. The bubbly pear-liquor concoction is named after the school marm in the classic children’s book Madeline by Ludwig Bemelmans, whose largest collection of works (including two original oil and pastel panels commissioned by Jacqueline Kennedy Onassis for the Christina O) are on display in the hotel. 

“The sand here is a perfect sugar white,” Witherell continues. “The surf is not overpowering, temperatures typically run 8 to 10 degrees warmer [than the outside air], but the real standout is the seclusion. Even in the height of the summer season, the beach here [East Beach] is never crowded. As for sunsets — watching the sun sink over the Watch Hill Lighthouse is absolutely spectacular — and in my opinion, the best in New England. I have explored the entire [northeast] coast — from Bar Harbor [Maine] to the Hamptons [New York], and truly nothing compares. And no, I’m not originally from Rhode Island.”

The Stay

Ocean House, Watch Hill

Photo by Shari Mycek

The History: The majestic Ocean House — instantly identifiable by its sun-yellow facade and white-trim exterior — was built by Captain George Nash in 1868 as one of seven (at the time) grand Watch Hill resorts. The hotel immediately captured the attention of high society, becoming instantly famous for catering to guests’ every whim — i.e., arranging grand balls with gleaming orchestras at a moment’s notice. As the other Watch Hill grand resorts slowly disappeared over time, Ocean House continued to welcome guests until 2003 when it was deemed beyond feasible repair and closed. In 2004, Watch Hill resident and current owner, Charles Royce, purchased the hotel with the intention of restoring it to its former grandeur. Where possible, he preserved the hotel’s original architecture (i.e. the circa 1868 stone fireplace was marked stone by stone and reassembled one by one); and painstakingly replicated the building’s original exterior design. Today, the incarnation features just 49 spacious guest rooms, 20 Signature Suites, and 8 Cottages (a dramatic reduction from the hotel’s original 159 rooms) — all of which pay homage to the property’s idyllic seaside location. Think tranquil sea blues and crisp whites, shimmering chandeliers, and subtle coastal (shells, starfish, coral) decor.

coral-fused dining room, penthouse suite, ocean house
Courtesy, Ocean House

On the Menu: As a designated Relais & Chateaux property, dining — from casual to fine — is superb. Summer finds guests on the beach, toes in the sand, at Théa at Dune Cottage, featuring a Mediterranean-inspired beachside menu, sweeping ocean views, and twinkle lights, or on the Verandah enjoying succulent lobster, local oysters, clams (shucked to order) at the hotel’s traditional New England raw oyster bar. Winter offers private tête-à-têtes inside faux fur-draped vintage ski gondolas, while year-round dining includes Bistro, famous for its OHBH (Ocean House meets Beverly Hills) salad, fresh seafood, and homemade pastas; and Coast, the hotel’s five-course, five-star, prix fixe tasting menu showcasing locally sourced seasonal produce and fresh-caught seafood, paired with fine wines. 

blue-and-white room, ocean house, Rhode Island
Courtesy, Ocean House

Best Bed: I loved my deluxe king room overlooking the sea (and Taylor Swift’s house) but for an even dreamier stay — and the same hypnotic sea view — ocean lovers will want to reserve the Penthouse Suite, featuring ocean views from every turn, a rooftop terrace overlooking the sea, formal dining area rich in coral, and soothing blue-and white bedroom hues, or the Tower Suite, complete with porthole-like windows, 360-degree water views, and a maritime-inspired spiral staircase. Likewise, art aficionados (and Madeline fans) will adore the Bemelmans Suite, featuring ocean views, light blue hues punctuated by yellow, eight original Bemelman art pieces, two baths, and a fireplace.

Wellness Bliss: Round out long beach walks, morning yoga and pilates, laps in the pool and long  soaks in the sea (or bathtub) with soothing spa treatments. While the spa menu is rich with facial and massage offerings, opt for the signature “Soothing Waves” incorporating customized massage techniques, which — in the case of my therapist, Christian — combined deep tissue with flowy stretching Thai massage. End it with a shot of the spa’s signature pomegranate-apple cider (a.k.a. ‘fire cider’) — a symphony of apple cider vinegar, pomegranate juice, jalapenos, garlic, onions, ginger, turmeric, honey, oranges, lemons, and apples — made in house daily.

Downtime: For a page turner, pick up a copy of Finding Mrs. Ford,” a novel set in Watch Hill, and written by Deborah Goodrich Royce, co-owner (with husband, Charles) of Ocean House.

Weekapaug Inn, Weekapaug

weekapaug inn, westerly, rhode island
Courtesy, Weekapaug Inn

The History: On the opposite side of Westerly — in the affluent residential community of Weekapaug and resting on the shore of Quonochontaug (saltwater) Pond — is Ocean House’s sister property, Weekapaug Inn, celebrating its 125th anniversary this year. The two hotels blended families in 2012 after Ocean House owner, Charles Royce, and longtime Weekapaug resident, Lang Wheeler, entered a partnership to restore and transform the inn into a year-round, low-key luxury destination. Prior to the affiliation, the inn had only one owner: the Buffman family. In 1899, Frederick Buffman and his wife, Phoebe, opened the then tiny inn on a spit of land between the ocean and saltwater pond. The Great Hurricane of 1938, however, completely wiped out the hotel (and surrounding homes) but the Buffman family persevered by rebuilding it away from the dunes (on its present-day site).   Encouraging fellow  homeowners to follow suit, the Buffman family forever protected  the barrier beach. Today, the natural beach scape is a haven for birds (heron, osprey, egrets, and the endangered piping plovers), flowers (hydrangea, asters, roses, beach plums), and waving marsh grasses. While the beach is largely void of people, guests are given privy access with loungers, shade umbrellas, and food service. Clamming the waters in front of the inn (rakes and muck boots provided), kayaking, sailing, and paddle boarding are other favorite pastimes, as is seal watching (by boat in late fall and by telescope from the lobby in winter). Reciprocity between Ocean House and Weekapaug Inn enable guests to shuttle between (Weekapaug guests may reserve spa treatments; Ocean House guests can engage in nature walks and safaris).

carriage house suite, weekapaug inn, Rhode Island
Courtesy, Weekapaug Inn

Best Bed: Overlooking the saltwater pond and complete with a fireplace and heated, soaking tub on the outdoor deck, the one-bedroom, 1.5-bath Carriage House Suite offers the ultimate relax. We love the light-filled space, crisp white Frette linens, and pops of blue tiles.  

weekapaug inn's famed clam chowder, rhode island
Courtesy, Weekapaug Inn

On The Menu: Within two months of reopening (in 2012), the Inn became a member of Relais & Chateaux, putting The Restaurant on the culinary map. Locals are now regulars and many guests admittedly come for the exquisite farm-to-sea-to-table dining experience. “We drove from Boston today just for chef’s scallops,” an elderly couple, one table over, told me. Chef Andrew Brooks is also known for his four-course tasting menus paired with wine, raw-bar starters (native oysters and Quonnie rock oysters), and signature Stonington scallops, short rib pappardelle, and Crescent Farm duck.

harp seal lounging on the beach, westerly rhode island
Photo by John Woodmansee, courtesy of Ocean House

Wellness Bliss: Clamming, stand-up paddle boarding, and kayaking are an integral part of the experience. But don’t miss a one-on-one outing with naturalist Mark Bullinger — be it birdwatching, a barrier beach walk, stargazing followed by s’mores around the firepit, or his Zen-like sunset jeep tour along the beach to the Watch Hill Lighthouse. Delightfully, New England weather is never an issue — Hunter rain boots and jackets are provided. 

Downtime: Sip cocktails by one of the Inn’s wood-burning fires, or head to the airy blue-and-white-hued ‘sea room’ for a game of Scrabble or Backgammon.

Other Must Dos in Westerly

Napatree Point Conservation Area 

napatree point, westerly, rhode island
Photo by John Woodmansee, courtesy of Ocean House

Open year round to the public, Napatree Point (which spans over a mile of beach) is home to many species of Rhode Island birds. Perfect for both walking and hiking, the beach is also dog-friendly in the off season.

Nana’s Westerly

I heard mention of Nana’s three times (including from the waiter who served the prized sourdough bread during dinner at Weekapaug Inn) before finally stepping into the small eatery in  ‘downtown’ Westerly. Loaves of fresh-from-the-oven sourdough bread lined the counter, along with must-try ‘sourdoughnuts’ — the cinnamon sugar version tasted just like my grandmother used to make every Faschnaut Day. 

St. Clair Annex Ice Cream

Owned by the Nicholas family for more than a century, St. Clair Annex in Watch Hill is a Westerly tradition. The cream is sourced from a local dairy; the ice cream is still handmade in small batches.

Flying Horse Carousel

flying horse carousel, watch hill, rhode island
Courtesy, Ocean House

A traveling circus reportedly abandoned the (circa 1876) carousel — said to be the only surviving flying horse carousel in the US — to Watch Hill in the 1920s (along with the real-life horse that pulled the carousel to make it turn). The hand-carved horses — with leather saddles and real tails and manes  — are not attached to the ground, but rather  suspended and “fly” while in motion. Only children (no one over 12 years or over 100 pounds) may ride.

Wilcox Park 

Listed on the National Register of Historical Places, this former ‘Victorian strolling park,’ replete with fountains and hidden gardens, is also the summertime home of Shakespeare in the Park performances by the Colonial Theatre.

Olympia Tea Room 

There’s no high afternoon tea on the menu. This family-owned bistro (which started as a soda shop) has been a staple in Watch Hill since the 1930s. Featuring carnation-pink walls, antique mahogany-carved booths, and black-and-white-checkered floors, the restaurant is known for its lobster rolls, linguini with roasted clams, craft cocktails, and extensive wine list. Arrive early as reservations are not accepted.

Classic Shopping

Visit Sea Bags for nautical tote bags made from recycled sails. And iconic Lilly Pulitzer for super colorful resort and beachwear.

Feature image courtesy of Canva