Holiday Weekend on Nantucket, Massachusetts | Weekend Away

A summer island warms to the off-season with the Nantucket Christmas Stroll one very special holiday weekend.

By Joe Bills

Oct 06 2020


A bedecked dory brings cheer to the Easy Street Boat Basin.

Photo Credit : Elizabeth Cecil

Editor’s note: This travel feature was reported and photographed in December 2019. Shortly after Yankee’s November/December 2020 went to press, the Nantucket Island Chamber of Commerce announced that the 2020 Christmas Stroll would be canceled due to COVID-19 concerns.

Nantucket Noel returns in 2021, running from November 26 – December 31. 

A bedecked dory brings cheer to Nantucket’s Easy Street Boat Basin.
Photo Credit : Elizabeth Cecil

Bustling beaches, sea captains’ houses, cobblestone streets lined with shops, and 13,000-plus acres of preserved land have long made Nantucket one of New England’s most iconic summer playgrounds. But the island doesn’t go away when the summer folk do.

Sure, more than half its homes are shuttered for winter, and some stores and restaurants close up shop when the crowds depart. Yet the slower pace makes Nantucket an idyllic getaway from late fall onward, its popularity peaking again in the holiday season, when its famed Christmas Stroll weekend fills the streets.

There are several ways to get to Nantucket, just 30 miles off Cape Cod, but none are simpler (or easier on the wallet) than the scenic one-hour jaunt from Hyannis on the Grey Lady IV, a high-speed ferry operated by Hy-Line Cruises. The ferries run on a reduced schedule in the winter months, so plan ahead.

The Nantucket Hotel & Resort’s glittering front entrance sets the mood for a holiday stay.
Photo Credit : Elizabeth Cecil

Holiday Weekend on Nantucket, Massachusetts


It’s less than a mile from the ferry dock on Straight Wharfto the Nantucket Hotel & Resort, our chosen lodging, and because cars are at a premium on the island, a reservation here includes shuttle service, which makes for an effortless arrival. While there certainly are other worthy overnight options, the Nantucket—originally opened as the Point Breeze Hotel in 1891 and recently renovated by current owners Mark and Gwenn Snider—is hard to beat for ease, history, and classic charm.

Once you’ve settled in, it’s time to find some sustenance. Remember that no matter where you are on Nantucket, you’re never more than four miles from the sea, and while that typically keeps the weather on the mild side (by New England standards, at least), changes happen quickly and winter breezes can be more than a little brisk, so dress in layers.

The island is made for meandering, and a 10-minute walk back toward the wharf takes you through the retail district, past shops and restaurants. Some eateries require reservations, but don’t fret if you haven’t made one: We had no trouble getting a table at B-ACK Yard BBQ, where chef Fred Bisaillon and his crew serve up melt-in-your-mouth barbecue topped with a choice of sweet, hot, gold, and vinegar sauces, which can be mixed and matched to your taste. (Can’t decide? Try the pulled pork shoulder with an even mix of hot and sweet sauces.) The Southern vibe carries over to the cocktail menu, whose concoctions include the Georgia on My Mind, a mix of bourbon, peach, and basil, and the Stevie Ray, a vodka drink with jalapeño, lemon, and cucumber.

A stroll back to the hotel puts a capper on the first day. Among the fringe benefits of an off-season stay are the portable fire pits on the porch, which invite guests to pull up a wicker chair and admire the evening for a while.

Classic duds at Murray’s Toggery Shop.
Photo Credit : Elizabeth Cecil


The Downyflake is a Nantucket institution,serving breakfast, lunch, and, most important, fresh doughnuts since the 1930s. Its mid-island location is a bit out of the way, but if weather permits, the half-hour walk is just what the conscience ordered to compensate for those warm sugar doughnuts.

Returning to town to visit the inviting shops of Main Street, start with a classic: scoring a pair of Nantucket Reds at Murray’s Toggery Shop, founded in 1945. At Sylvia Antiques, located in the historic Pacific Club building, you’ll want to linger over authentic Nantucket baskets and all manner of other vintage treasures. And a stop at Mitchell’s Book Corner provides the opportunity not only to pick up the latest best-seller or a classic read, but also to explore a well-stocked local books section, where a wealth of island knowledge awaits. As you work your way back toward the hotel, make sure to detour to Current Vintage on Easy Street, where retro clothing and curated wines make for an odd but wonderful pairing.

Nautical decor at Sylvia Antiques, which has been owned by the same island family for more than 90 years.
Photo Credit : Elizabeth Cecil

A few minutes’ walk from Easy Street brings you to the Nantucket Whaling Museum, a monument to the sailors who once made the island the whaling capital of the world, the industries their dangerous work supported, and the families they left behind while at sea. From the 46-foot-long sperm whale skeleton to the massive lever press from the Hadwen & Barney Oil and Candle Factory, the museum’s exhibits bring to life the large-scale realities of the hard labor and incredible sacrifices that built the island.

Even in the off-season, Nantucket offers up more great dining options than can be experienced in one weekend, so prepare for tough choices. At Breeze, conveniently located in the Nantucket Hotel & Resort, chef Albert Cannito creates classic dishes from local ingredients—and since November and December are scalloping months here, delicious seafood abounds. You’ll want to savor the seafood stew (mussels, scallops, cod, and lobster simmered in tomato broth), but if your tastes are geared inland, the crispy fried Brussels sprouts and mushroom ragout gnocchi are pretty darn good, too.

For evening entertainment, check out the lineups at the film and cultural center Dreamland and the White Heron Theatre, where A Nantucket Christmas Carol (which reimagines Ebenezer Scrooge as a whaling captain) is a seasonal staple. Side note: Behind the Dreamland, a tiny park is being built to honor children’s television icon Fred Rogers, whose family summered in Madaket for more than 40 years. The park’s centerpiece will be a life-size statue of “Mister Rogers”—dressed in his famous cardigan sweater—by sculptor and summer resident Seward Johnson. Don’t miss the photo op!

Strolling Nantucket’s famed cobblestone streets.
Photo Credit : Elizabeth Cecil


Pack your bags early and arrange for them to be dropped off at the ferry, then take some time to lounge on this final island morning—maybe bringing one of your new books to Handlebar Café on Washington Street and lingering over a latte or a terrific nitro breakfast tea.

There’s more to Nantucket than just the retail district, of course, and there’s no better way to see it all than with seventh-generation islander Gail Nickerson Johnson of Gail’s Tours, who offers both standard and customized tours lasting a little under two hours. From the gorgeous inner-island preserve to historic structures like the Old Gaol, the Greater Light, and the Old Mill, she’ll share plenty of backstory and insider lore, and point out the homes of the rich and famous along the way. The most memorable stop, without question, is on Nantucket’s east end, where the rapid erosion of 90-foot coastal bluffs is a reminder of how vulnerable an island’s beauty is to the power of the sea.

To put an exclamation point on your island experience, head to the Nautilus, where the small-plates menu includes tempura oyster tacos, blistered shishito peppers, and Nantucket bay scallop tostadas, made with scallops that very likely were still in the water when you arrived. From the restaurant, it’s just one final short stroll to the wharf where the Grey Lady awaits. 

Patrons gather at the Nautilus, where dishes are designed for sharing.
Photo Credit : Elizabeth Cecil


Since many event organizers and local businesses are adjusting their operations in response to COVID-19 health concerns, please contact them directly or check their websites before making travel plans.

More Photos from a Holiday Weekend on Nantucket

Holiday wreaths greet visitors at the historic First Congregational Church of Nantucket.
Photo Credit : Elizabeth Cecil
At the Nantucket Hotel & Resort, a 1934 bus stands ready to shuttle guests to the ferry.
Photo Credit : Elizabeth Cecil
A hearty breakfast plate at the Nantucket Hotel & Resort.
Photo Credit : Elizabeth Cecil
Fresh-made Downyflake doughnuts are a must for any Nantucket visitor.
Photo Credit : Elizabeth Cecil
A welcome sight for local bibliophiles on Main Street, Mitchell’s Book Corner also has a sister shop, Nantucket Bookworks, just a few blocks away.
Photo Credit : Elizabeth Cecil
A detail of a cetacean mobile at the Nantucket Whaling Museum.
Photo Credit : Elizabeth Cecil
A view of Main Street, which retains its local flavor thanks to a ban on big chain stores.
Photo Credit : Elizabeth Cecil
Gifts for the whale lover at Sylvia Antiques.
Photo Credit : Elizabeth Cecil