The happy luxury of the Nantucket Christmas Stroll

Sure, you could visit a glittering city like New York, London or Paris during the Christmas season. But sometimes its nice to dream of a different kind of Christmas. One near the sea, with old weathered clapboard buildings, and hand-decorated trees. One with nutcrackers of a different sort. One like Christmas on Nantucket. This small and special island off the coast of Massachusetts is best-known as a summer retreat. But those who love it also know about the annual Nantucket Christmas Stroll.

what’s it like at Christmas on Nantucket?

Well, dear reader, for many people it’s just three words: The Christmas Stroll (actually, for the locals, it’s just one word: “Stroll”). In our endless pursuit of modern luxury, we dispatched our Staff Photographer to the island to snap some pictures so that we can all see firsthand what this legendary Stroll is really all about.

How did the Christmas Stroll get started?

In 1973, the local merchants on Nantucket brainstormed ideas to prevent residents from journeying to Cape Cod to do their holiday shopping.

That year, in an effort to get people to shop local, stores stayed open late the first Friday in December. That initial Stroll lasted for only three hours. The shopkeepers provided free wine, hot chocolate, tea, mulled cider, fruitcake, and holiday cookies. And the shoppers filled their cars with local crafts, books, clothes and other holiday gift items.

The annual Christmas Stroll was born. Stroll Saturday on Nantucket is always the first Saturday of December.

what was this year’s theme?

The theme of the 45th Annual Christmas Stroll was “A Beautiful Stroll in the Neighborhood.” The theme was chosen to commemorate the 50th Anniversary debut of Mister Rogers Neighborhood on PBS. Fred Rogers was a longtime island resident. His “Crooked House” in Madaket is a historic island landmark.

what does the island look like for the Christmas season?

It’s charming. The merchants and restaurants on Main Street get decked out in their festive best. For example,  ACK 4170 is filled with unique gifts and jolly decor.

Dozens of decorated Christmas trees line Main Street, each decorated by a local shop.

Every year a local artist or decorator is chosen to adorn the huge 20-foot tree at the top of Main Street, a tree that “magically” talks to all who visit it during Christmas Stroll Saturday. Chat with the large Christmas tree at the top of Main Street, and it will answer!

In the waters just off Easy Street, every year there’s a miniature Christmas tree nestled in a dinghy. It’s an iconic image of this annual celebration.

what happens during the Christmas Stroll?

1. Singing

Carolers in costume sing familiar holiday tunes at various downtown locations. A variety of live entertainment is offered in the middle of Main Street, which is closed to traffic for the day. Toward the end of the afternoon, there’s a Christmas Stroll community carol sing-along.

2. Shopping

There are surprise sales and soirees occurring throughout the day. There’s a Christmas market at St. Paul’s Church. You can make your own Christmas wreath, decorated with seashells, pine cones, and lots of glitter. The “must have” souvenir each year is the exclusive Made on Nantucket Stroll Ornament with the year of your visit on it.

3. Sipping

Many merchants offer holiday refreshments to shoppers. There are special dinners at island restaurants. Grab a bite to eat during the day at the Nantucket Hotel. Have a Stroll Spritz.

4. Strolling

You can take a walk on Main Street – and also one off the beaten path. On Stroll Saturday, families can take a free guided winter walk hosted by the Nantucket Conservation Center through a hardwood forest that extends to the shores of West Polpis Harbor, with opportunities to see herons, egrets, and shellfish.

what should one wear to the Christmas Stroll?

Well, on the opening day of Stroll, there’s a day-long Ugly Sweater Competition. The winner gets a 75% discount at a local clothing store. Which makes perfect sense.

Lots of people “dress in theme,” with reindeer antlers, poinsettia crowns, Santa hats or even full-body Nutcracker suits. And of course, their canine companions do, too.

is santa involved in this?

But of course. Midday on Stroll Saturday, the Nantucket Town Crier, in full regalia, rings in The Annual Christmas Stroll. Then he leads the crowd to Straight Wharf to watch Santa arrive via Coast Guard cutter.

Santa and Mrs. Claus hop on an antique fire truck, and everyone is invited to join the parade as it travels up Main Street and across Centre Street to the Jared Coffin House. There, Santa visits with children for a couple of hours, while the elves distribute candy canes and hot chocolate.

what’s the festival of trees?

Each December, the Nantucket Whaling Museum is transformed into a glittering winter wonderland by the Nantucket Historical Association. The Annual Festival of Trees showcases more than 80 Christmas trees designed and adorned with unique decorations.

where’s the best place to stay?

The White Elephant is the best-known hotel on Nantucket. Each year, the hotel offers a Christmas Stroll package. In 2018, it included two festive scarves, in-room mistletoe, a Nantucket Sleigh ride, local wine, and daily breakfast for two. Rates start at $2,145 for three nights.

If you want a more residential feeling, stay at the White Elephant Loft at 32 Main Street, which offers guests direct access to Nantucket’s downtown area. This 2,500 square foot pied-à-terre-style loft is located on the 2^nd floor of a 19^th -century brick building, featuring a gourmet kitchen and keys to a BMW hybrid-SUV for use during the duration of your stay.

An interesting alternative is the boutique hotel Greydon House. It’s cozy and charming, with a pine-paneled reception area and snug sofas in the library. The space was designed by chic Manhattan firm Roman and Williams. Chef Marcus Gleadow-Ware helms the hotel’s restaurant.

we love this idea

The smell of the sea, the cheerful decorations and the festive spirit – it’s a different kind of holiday than what many of us may be accustomed to. But Christmas on Nantucket looks really fine to us. Maybe next year.

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