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Travel: Come, Let's Stroll in Nantucket

Travel: Come, Let’s Stroll in Nantucket
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Photo Credit: Carl Tremblay

View the Slide Show: Nantucket Holiday Stroll.

My first trip to the island of Nantucket was in the 1970s. My little sister was a toddler, and my older brother was spending the summer with family friends on a ranch out West. My mother sensed that I was a little jealous of both the cute baby and my big brother’s adventures, so she packed us up for a long girls’ weekend. We took the ferry from Hyannis and spent the weekend eating ice cream, visiting the Whaling Museum, swimming at Children’s Beach, riding bikes out to ‘Sconset, and window-shopping. I spent the return trip working on a needlepoint pattern that Mom had bought me and admiring my excellent sunburn.

That was the first of many trips to an island that captured my heart decades ago, as it has those of the many thousands who spill out of the ferries and fill its cobblestone streets. With its beautiful beaches, outstanding sailing, vibrant shops, and waterside dining, it’s so easy to fall in love with Nantucket in the summer.

But there’s another Nantucket. Come fall and winter, it’s a sleepy New England village. It belongs again to the locals, and to the hardy souls who love walking its windswept shores with no one in sight, who duck into its warm restaurants, where everyone seems to know everyone else. There’s one special weekend in December, though, when the streets hum with visitors again. Officially it’s the annual Christmas Stroll Weekend–though locals call it simply “Stroll.” It began 37 years ago, and the idea hasn’t changed since: Give people a reason to get together, to enjoy the island, to give a big boost to its shops and restaurants, and to celebrate a place that doesn’t close up when the air turns cold–it simply relaxes, and in a way its people grow warmer. Stroll brings together people in a good mood, inspired in part by festive shops decorated with holly boughs and fanciful window displays.

We arrive by high-speed ferry on Friday, and the spirit of the weekend ignites suddenly as we spy a giant wreath hanging from Brant Point Lighthouse, then boats across the harbor decorated with Christmas trees on their bows and colorful lights strung up their masts. Greetings at the Straight Wharf dock seem more heartfelt than in the summer months–there’s less baggage, less bicycle chaos, more hugs and laughter.

The Nantucket Whaling Museum never gets old for me, so our first night begins here. The museum was renovated in 2003-2005, creating an even more attractive setting for the historical and cultural displays highlighting the island’s past as a whaling community. There’s nothing abstract here. When you see the 46-foot-long skeleton of a sperm whale hanging above, you know what it feels like to be dwarfed by nature in all its awesome power. All around you is evidence of the islanders’ life before tourists came ashore. There’s exquisite scrimshaw on display in the many glass cases, along with lightship baskets and other period folk art.

But this is Stroll Weekend, so the year-round items share space with the annual “Festival of Trees”–a big deal on the island now, with some 70 holiday evergreens decorated by local merchants, nonprofit organizations, and individuals. Most trees are tasteful, themed expressions of Christmas; others are cheeky cultural commentaries–such as one draped with ornaments of empty prescription bottles of Prozac and Viagra. In yet another room of the museum, a hush falls over the gathered audience as a slightly giddy group of fresh-faced high-school students file up onto risers and in perfect harmony charm the crowd with holiday favorites.

Outside, the streets are teeming with revelers in just the mood you’d expect. The spell of the season is clearly in the air: men in red corduroys, plaid vests, and Santa hats; women in elf costumes; others wrapped head to toe in white blinking lights; dogs adorned with reindeer antlers (not sure what their mood is). But that’s just the Friday-night warm-up. Tomorrow will bring Santa and Mrs. Claus–and no summer celebrity sighting compares.

On Saturday, Santa arrives in style–who needs reindeer when you have a trusty Coast Guard cutter? Closer, closer, with Mrs. Claus by his side, the big guy greets the throngs of jumping and clapping children at Straight Wharf. Tugged along by the town crier, the Clauses hop into a horse-drawn carriage, and off they go, parading down Main Street, escorted by carolers in Victorian costume, all the way to Pacific National Bank, where kids get to chat with Santa and a “Magical Talking Tree.” Yes, the scene oozes with charm and joy, but it’s not manufactured–this is the real deal. The crowd is all ear-to-ear smiles, and the good mood is infectious. Just look at the wide-eyed faces of the youngest toddlers, the adults not embarrassed to be feeling this happy.

Most shops and restaurants are happily open, too, and feature holiday-theme window decorations, one more extravagant than the next: Christmas trees made of scallop shells, wreaths and ribbons of every sort. The welcoming aroma of hot toddies and warm cinnamon from freshly baked cookies wafts over us. It’s a charismatic way to experience a little bit of an old-fashioned Christmas.

And, if you need a practical excuse, you can get some early shopping done without going to a single mall. Nantucket’s retailers look forward to this big push to get through the rest of the long winter season, and local crafters get into the act with shows and demonstrations. At the Preservation Institute, St. Paul’s Church, and St. Mary’s Church, artisans are lined up in rows, displaying handcrafts ranging from ornaments and greeting cards to jewelry and clothing to foods and toys. It’s hard not to spend, whether you’re looking for a stocking stuffer carrying a reminder of a fun weekend or a more exquisite purchase to last a lifetime.

Goodwill goes only so far, of course. All that shopping and smiling can certainly build up an appetite–and islanders don’t forget how to make great food when the days turn colder. In the parking lot of the Grand Union market, right off Old South Wharf, the Nantucket Chamber of Commerce sponsors an event called “Chamber Food Fair,” as local professional chefs and home cooks offer hot provisions to chilled and weary shoppers.

Serious dining is available as well; in fact, many restaurants re-open for Stroll Weekend. Finding a seat at one of the island’s many great venues requires patience and, better yet, some planning, but you’re bound to make new friends or even join the roaming carolers while you wait. Despite the chilly weather, the Boarding House restaurant’s outdoor oyster bar keeps the crowds pleased well into the afternoon.

As the early-winter sun slips toward the horizon, the caroling continues, and theatrical performances begin. Stage and screen actor John Shea reads Dylan Thomas’s classic A Child’s Christmas in Wales; the Karina Association presents its “Christmas Opera Concert.” And, if you feel the need to slip away from all this Noel activity for a bit, there’s still plenty of island left: house tours, literary and historical walking tours, book signings, birdwatching, wine tastings, a ghost walk, and Saturday’s annual five-mile “Nantucket Winter Run.”

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Updated Sunday, December 1st, 2013

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