The first weekend in December is a delightful time to be on Nantucket. That’s when the island hosts its annual downtown Christmas Stroll and takes on the look of a Norman Rockwell painting come to life. The handsome brick and granite buildings in historic downtown are decorated with evergreen roping, swags, and wreaths, their tall windows sparkling with lights as shopkeepers set out elegant spreads of wine, fruitcake, holiday cookies, mulled cider, and hot chocolate to welcome shoppers.
The tradition of the stroll began forty years ago as part of the Chamber of Commerce’s month-long celebration, Nantucket Noel, and has steadily grown in popularity; today, the Christmas Stroll is an internationally renowned holiday event. The joy of giving (to family, friends—and oneself!) is fully evident as shoppers spend on lavish items in world-class shops for one-of-a-kind artisan pieces for the home, or on apparel, jewelry, books, art, and other spectacular items.
Preparations for the Christmas Stroll begin weeks earlier; the day after Thanksgiving volunteers line the downtown streets with hundreds of seven-foot Christmas trees packed with decorations. Then, during a caroling ceremony at dusk, the trees are illuminated to the oohs and aahs of small children (and their taller friends). It’s a magical sight no matter your age or how many times you’ve been present for it.
At the top of Main Street, a twenty-foot Christmas tree—visible from blocks away thanks to the elevation—is the holiday season’s landmark for visitors.
Dozens of beloved traditions and festivities make the Christmas Stroll weekend truly special. On Saturday, carolers in costume sing holiday tunes at locations throughout downtown. Main Street, which is closed to automobile traffic for the day, is the site of artisan crafts’ shows, holiday-themed performances, and artists’ exhibitions. Midday on Saturday, the Nantucket Town Crier, dressed in full regalia, rings his bell and leads everyone to the wharves to meet Santa and Mrs. Claus, who arrive via Coast Guard cutter and then head to the Jared Coffin House to meet with children.
Even the famed Nantucket Whaling Museum is transformed into a glittering winter wonderland with its Festival of Trees showcasing nearly one hundred Christmas trees, each one adorned with unique decorations by island businesses.
CRU reopens for the Christmas Stroll for four days (from the Thursday before through Sunday), beautifully decorated for the season and serving a decadent all-day brunch every day. Chef Erin unveils a special menu of holiday-inspired dishes for the weekend including CRU’s favorite: Nantucket Bay Scallops. After a day of shopping, a glass of hand-selected wine or a seasonal CRU cocktail (iced or warm) is perfect for cozying up by the CRU fireplace where you can relax and ponder the rest of the treasures you need to purchase during this special annual tradition on magical Nantucket …
Buttermilk Soufflé Pancakes with Pecan-Date Butter and Maple-Roasted Bananas
Potato Pancake with Horseradish Crème Fraîche
Winter Fruit Salad with Passion Fruit Vinaigrette
Eggs Baked with Spicy Tomato Broth, Chorizo, and Swiss Chard
It might seem contradictory that a small, remote island known for its rustic natural beauty (and whose residents are proud to maintain and protect more than thirty miles of bike paths) would also be home to stores that cater to the most discerning buyers of high-end art, one-of-a-kind pieces of jewelry, artisan crafts, clothing, and home décor. Yet that contradiction is exactly what makes Nantucket so appealing and unique.
Strolling historic downtown Nantucket to shop is a wonderful way to spend an afternoon. You’ll find street after street of enticing boutiques, galleries, and cafés side by side, each one welcoming you with attractive windows and entries. A good place to start is with a walk up Main Street from the waterfront, meandering the side streets as you go.
BODEGA NANTUCKET, 2 CANDLE STREET
A beautifully curated selection of home accessories, glassware, jewelry, and furniture with the perfect mix of modern and coastal. This shop is sure to provide the ideal hostess gift, addition to your new summer home, or a beach-inspired reminder to bring home to the city.
NANTUCKET LOOMS, 51 MAIN STREET
This iconic island boutique is best known for its sumptuous hand-loomed blankets and throws—most of which are created in the building’s second-floor loom room—of linen, wool, or cashmere. The designs are modern yet timeless, and the colors are evocative of the ever-enchanting Nantucket landscape. These hand-woven items are the perfect complement to their selection of the work of more than 80 local artisans including ceramics, artwork, and furniture.
MILLY & GRACE, 2 WASHINGTON STREET
Named after her grandmothers, the owner, Emily Hollister, curates her collection to highlight a balance of contemporary and classic clothing perfect for island life. Feminine dresses, delicate blouses, and cashmere wraps are the cornerstone of this boutique with dashes of home accents and gifts mixed in with just the right amount of surprise.
ATLANTIC, 18 FEDERAL STREET
Longtime summer resident Colleen Darby Wurts originally started her business in a friend’s ’Sconset garage. Now, her lofty, open space on Federal Street is a whimsical collection of clothing, art, antiques, and accessories to complement any home collection.
CURRENTVINTAGE, 4 EASY STREET
Owner Elisabeth English is known for her keen eye in vintage shopping including an epic hat collection of vintage Lilly Pulitzer (for women and men). As the weather turns colder, be sure to look for fur-trimmed coats, holiday sweaters, and of course, the perfect bottle of wine.
NANTUCKET BOOKWORKS, 25 BROAD STREET
This island institution is the epicenter of all that goes on in the world of books on Nantucket. Every turn you make in this cottage-like store reveals more treasure.
SAMUEL OWEN GALLERY, 46 CENTRE STREET
This contemporary art gallery is committed to exhibiting the work of emerging artists with rotating exhibits. You won’t want to miss the latest pieces.
EPERNAY WINE AND SPIRITS, 1 N BEACH STREET
This wine store has an expansive collection of fine wines, champagnes, and spirits. A must-stop on your way to Step’s Beach for the perfect sunset picnic or to stock up before an afternoon sail. Owners Jenny Benzie and Kirk Baker are always on-site to help you select the perfect wine for your vacation.
This list of shops and galleries is the tip of the iceberg. Come and check out Nantucket—during the Christmas Stroll or any other time of year—and see why people make this small island a shopping destination.
