Falling for Nantucket

BY Ottocina Ryan

Nothing beats sunshine on palm trees year-round, but there’s something about flipping the calendar page to September that makes me crave coziness, crisp air, and the sound of boots crunching fiery leaves along cobblestone streets. Not wanting to forsake coastal charm for a New England fall entirely, Nantucket was the perfect destination. Though I lived in Boston for three years, my first visit to the quaint island off of Massachusetts was this past autumn.

With my friend’s list of recommendations in hand, I arrive at the Wauwinet Hotel. The beachfront gray-shingled building, adorned with white trim, is set outside of town, surrounded by open fields and forests. Fun fact: half the island is conservation land. Tonight’s dinner is at Topper’s, named after the original owner’s Welsh Terrier. Retsyo oysters harvested just 300 yards from our table prelude a decadent carbonara covered in truffle shavings and, to wrap up, a pumpkin parfait dessert in keeping with the season’s theme.

In the morning, I open my shutters to a view of the manicured lawn and, just beyond, the ocean. I tuck back into bed with room service pancakes and watch the waves. Called to the shore, my friends and I take the hotel’s complimentary BMW X7 out to Great Point Beach to explore one of the island’s three iconic lighthouses. I soak up views scattered with shells, gray seals, birds, and polished homes. In the summer, it’s packed with people. Locals repeatedly insist that fall is the best time to visit; the temperature is still in the 60s, but the crowds are long gone.

“I soak up views scattered with shells, gray seals, birds, and polished homes. ”

We walk along an unimaginably quaint street made of crushed oyster and clam shells, gazing up at shingled homes with names like Pipe Dreams, Snug Harbor, and Hedge Fun. Gardens of hydrangeas and trellised roses seem like a requirement, appearing everywhere we look. On the walk, we pass a home with a whale topiary, spout and all. Nature isn’t the only thing preserved on the island. Rather than tearing down houses, they move them. If the walls could talk, they would tell stories of actors migrating to the island in the 1880s, cranberry bogs, and the rugged whaling industry. The uniform structures trace back to Quaker roots, where everything was equal. Now it’s just aesthetic.

For the rest of our time on Nantucket, we move to The White Elephant to be closer to town. Each aspect of the hotel is its own item on my list of recommendations, and I can see why. My suite opens to a patio with a sweeping view of the harbor: an irresistible spot for reading or a morning coffee. Even in October, the weather is pleasant enough to soak up the autumn sun on a wicker chaise, and cozy enough to ignite my living room fireplace in the evening.

Dinner is naturally at Brandt Grill, the onproperty restaurant. A round of White Elephant cocktails—essentially a tequila piña colada— starts a night of long conversations and endless laughter. The salad with truffle vinaigrette is the most memorable salad I’ve ever had. Still, the pasta special is the star of the show—fettuccini swirled with hefty lobster claws, bacon, and a poached egg, all drizzled with duck fat from a candle. Decadent would be an understatement.

Main street, where each shop and restaurant is more idyllic and charming than last, is just a five-minute walk away. Lily Pulitzer, Veronica Beard, and Polo Ralph Lauren commingle with contemporary boutiques like Wheat. Brick and slate sidewalks—homeowners are responsible for the sidewalk in front of their house—line cobblestone streets. Better yet, the quintessential New England town is small enough to put away the Maps app after a couple of days. It’s like something out of a movie.

We spend the week making our way through recommendations. The Green Market for smoothies, gourmet grab-and-go, pretty tableware, and clean beauty products. Lemon Press for shrimp saffron lettuce wraps and extensive açai bowl offerings. The Whaling Museum to immerse ourselves in the island. A sperm whale skeleton that washed ashore in 1997 anchors the museum, while the surrounding rooms detail the island’s rustic history of whaling and candle making. Tap Room for a classic menu beginning with popovers and finishing with sticky toffee pudding.

One afternoon we take White Elephant’s complimentary bicycles to Cisco Brewery. The 20-minute bike ride takes us through residential neighborhoods and forested paths. It seems half of the island is at the brewery, dogs in tow, sipping beer flights and rosé from Nantucket Winery, grazing on lobster rolls and pizza from the various food vendors. Community is strong here, but everyone is welcoming as ever.

Back in town, I walk to an ice cream shop my friend promises is the best ice cream ever, eager to follow through on her instructions to get a mud pie and orange cream. Yet, it’s closed for the season. It’s the only moment I wish I’d made it to Nantucket earlier in the year, and for the hundredth time, I wish I’d gone 14 years sooner. *