If someone had suggested I spend two months on Nantucket in the dead of winter, I’d have raised an eyebrow. And yet here I am. Nantucket — often heralded as the hydrangea-laden jewel of the summer social circuit, where streets buzz with lobster-embroidered shorts and Lilly Pulitzer-clad vacationers — is typically deserted once the temperatures drop. But I quickly discovered that once the crowds disperse and quiet permeates the air, this charming island reveals an even richer, more intimate allure.
But first, where are we eating? Nantucket’s culinary reputation is legendary, so I was curious to see how it would fare when many establishments close their doors until spring. While it’s true that several beloved spots hibernate through the winter, what remains open is exceptional.
The Brotherhood of the Thieves is a cozy, old-world pub where dark wood panels and crackling fires create the perfect ambiance to fend off winter’s chill. Do not — I repeat, do not — skip the clam chowder, a creamy, briny delight that is every bit as comforting as a cashmere sweater.
Fusaro’s is a family-owned Italian gem tucked quietly into the island’s tapestry and still maintains its authenticity through dishes inspired by Sunday meals at Nana’s. The whipped ricotta starter is sublime, a creamy, airy cloud drizzled with honey and toasted almonds. As for the carbonara? Let’s just say I returned more times than I care to admit.
Of course, no off-season visit would be complete without frequenting Lola 41, the island’s famed hotspot, typically unattainable in summer without a reservation made well in advance. Come winter however, Lola’s doors swing open easily, offering the same outstanding sushi rolls, delectable smash burgers, and inventive cocktails, but sans the throng of fashionable diners jostling at the bar. Lola’s themed nights — Rib Night Wednesdays, Smash Burger Thursdays, and Sushi Sundays — became beloved rituals, cementing my newfound appreciation for Nantucket’s off-season rhythm.
Venture Outside
Winter on Nantucket shouldn’t be a deterrent, but rather an invitation to see that beloved scenery through a new lens. While summer might charm with sun-drenched beaches and flower-dotted streets, winter reveals a quiet beauty, equally captivating. A stroll through the heart of town, normally bustling with shoppers clutching bags and iced coffees, transforms into a serene meander through cobblestone streets lined with historical charm. I found unexpected joy strolling down Easy Street and wandering along Old North Wharf, where America’s oldest operational oyster house sits quietly dignified, a reminder of Nantucket’s maritime past.
One particularly enchanting morning took me across the island to Siasconset, known simply as ‘Sconset’ to locals. Armed with a vanilla-bean collagen latte from Roastd (my personal favorite coffee purveyor), I embarked on the Siasconset Historic Bluff Walk. The path, winding along cliffs high above the Atlantic, offers dramatic views and quaint, shuttered beach homes silently dreaming of summer. The absence of other visitors lent a sense of private magic, as if these gray-shingled homes were showing off just for me. This walk swiftly became a cherished routine, each time leaving me with fresh daydreams and a new Nantucket beach cottage I was decorating in my mind.
Feeling adventurous, I headed to Wauwinet for an off-road beach picnic. This required deflating my tires — a task reserved for those experienced in Nantucket’s peculiar beach-driving protocol — but the reward was a private stretch of sand, breathtaking views, and utter solitude. My advice? Don’t shy away from the adventure — just prepare accordingly. That means a sandwich from Walters and a good playlist.
When not outdoors, the island’s quieter months also offer the luxury of leisurely exploring Nantucket’s exceptional shopping scene. Murray’s Toggery, the quintessential Nantucket shop, never disappoints, especially when you can browse at your leisure, avoiding the summer rush. Winter sales add irresistible appeal, transforming casual browsing into fruitful treasure hunting.
Erica Wilson, chic and dreamy, the mother of modern-day needlepointing, is always a crowd pleaser thanks to stylish interiors filled with impeccably curated selections of clothing and home goods. But it was Nantucket Looms, with its iconic storefront right on Main Street, that truly captured my heart. Known for luxurious, handwoven textiles and a meticulous curation of locally made art and furnishings, the Looms encapsulate Nantucket’s artisan spirit. This past spring, the Looms released its first book, a tribute not just to their storied history but also to the stunning island homes adorned with their textiles.
On quieter afternoons, house gazing became a delightful pastime. Baxter Road and Cliff Road are prime areas to admire architectural gems ranging from historic saltboxes to grand waterfront estates, each exuding charm enhanced by winter’s quiet, overcast elegance. The absence of foliage allows architectural details to shine more clearly, making house gazing a surprisingly compelling off-season activity.
Velvet-Rope Moment
For an insider look on this tony island, schedule an appointment to tour Ten Easy Street, a concept showroom-meets-shoppe house designed by New York-based interior designer Eileen Kathryn Boyd. Get an off-season sneak peek at the house everyone is clamoring to get inside by Daffy Weekend. Once inside, enjoy a house glass of Pierre Jouët as you shop from one room to the next — each space thoughtfully layered with Boyd’s signature exuberant palette and curated mix of vintage and custom homewares. And if you’re craving a heat-wave moment, don’t miss the KLAFS sauna in the Lavender Haze Lounge.
Ten Easy Street isn’t just a design destination — it’s a lifestyle manifesto, and off season is the perfect time to soak it in without distraction. Between the playful palette, layered textures, and ever-evolving selection of artists and cutting-edge home tech on display, you’ll feel as though you’ve been granted a backstage pass to the best-kept secret on the island. Be sure to plan ahead for this one and schedule your private tour sooner rather than later.
Let’s Call It a Night
While you probably won’t be relaxing in The Brant’s new plunge pool — though the thought is a nice one — there’s still plenty of luxury to be savored at this stylish boutique property in Brant Point. Located just a short walk from town and mere steps from the beach, The Brant embraces the off season with the kind of ease that makes winter feel like a deliberate choice rather than a compromise. From the warm service to thoughtful details — plush linens, soft throws, and baskets for beachcombing walks — the hotel feels like a calm cocoon. Each morning begins with a complimentary continental breakfast (fresh croissants and strong coffee, naturally), and there’s a fleet of bicycles on standby should you want to cruise through the quiet streets or along the shore. While the summer crowd comes for the scene, the off-season guests of The Brant come for the stillness. The sense of escape is real here, and it lingers long after you’ve checked out.
My two months passed quicker than expected, each day solidifying my affection for the quieter Nantucket. What began as a tentative exploration became an immersive discovery of an island whose off-season magic rivals its bustling summer charm. The Nantucket off season might lack those iconic blooming hydrangeas, but it blossoms in quieter, subtler ways that left a lasting impression and, perhaps, even a preference. So, pack your sweaters, embrace the chilly breeze, and venture to Nantucket when others wouldn’t think to. You’ll find a place that’s just as delightful — perhaps more so — when it’s at its quietest.
Feature image, courtesy of Dan LeMaitre
