Sponsor Content

How to Have an Incredible Holiday Season on Nantucket

/ RP Photography

Nantucket is regarded as the ultimate New England destination for summer getaways, so Bostonians may be pleasantly surprised to hear that it only gets better in the off-season. Even in brisk and snowy weather, people have made holiday journeys across the Nantucket Sound for years to experience the beach-town charm in all its holiday glory—namely, for a long-held Nantucket tradition.

The Nantucket Christmas Stroll Weekend has graced the main streets of the beloved island for 48 years, and this year is the 49th Nantucket Christmas Stroll Weekend, from Friday, December 1 to Sunday, December 3. There will be a full schedule of island traditions to partake in, plenty to eat and drink, and no shortage of holiday spirit to celebrate—with Nantucket as the backdrop.

You can even plan to begin your holiday Nantucket stay at Thanksgiving, which will allow you to settle in and absorb the magic of the Nantucket winter—and catch a stunning Annual Christmas Tree Lighting Ceremony. We’re here to give you an early-bird look at how to make the most of it all.

/ Bill Hoenk Photography

The Christmas Stroll

The Nantucket Town Crier—a centuries-old unofficial role on the island—will kick off this year’s event on Friday by announcing Santa’s arrival by boat. The event’s nearly 50-year roots in Nantucket come from its predecessor, “Christmas Shoppers Stroll,” which began in 1973 on the first Friday of December as a way to keep locals on the island for their holiday shopping instead of traveling. Stores would stay open late to accommodate a special night of holiday shopping.

Today, local retailers are still the main attraction of a bigger, more developed Christmas Stroll, decorating their storefronts and participating in the Chamber’s tree decorating.

Those businesses will also contribute to a lineup of Stroll Saturday’s festive activities, such as cookie decorating, walking tours, book signings, hikes, special in-store promotions, performances, and receptions. Santa’s Village Marketplace will also make its annual appearance in the downtown area to offer food, crafts, and beverages. There will even be a special appearance by Santa.

Planning Your Trip to Nantucket

If you’re wondering when to book travel, here’s an insider tip: The Christmas Stroll may not be happening until December 1, but the iconic 20-foot tree lighting is on November 24 as part of the annual Nantucket Noel event. If you’ve been looking for a reason to stay on Nantucket for a full week, this could be your sign—the magical ceremony is not to be missed. And, if you can stay longer, Theater Workshop of Nantucket is putting on Elf the Musical at Bennett Hall on November 21.

As far as getting to Nantucket, many regulars know the drill. But for island newcomers, there are a handful of different ways to get to Nantucket; the ferry from Hyannis is the most popular way for New Englanders to make the 30 mile trek there. Hy-Line Cruises and Steamship Authority run year-round, so you can count on those high-speed catamarans and traditional car ferries to get you across the Nantucket Sound.

For friends and family traveling from far away, Logan Airport may be your best bet—but Nantucket also has the second-busiest commercial airport in the state, so for added convenience, out-of-towners can opt for a flight to Memorial Airport with flights through Cape Air, Tailwind Air, Tradewind Aviation, Gull Air, or FlyExclusive.

/ Charity Grace Photography

Staying on Nantucket 

To make the most of your holiday visit to Nantucket, you’ll want to fulfill your cozy hotel or bed-and-breakfast visions. But no matter if you’re in search of a whaling-era inn or a luxury hotel, book soon—The Christmas Stroll Weekend draws a crowd every year.

If you dream of a cozy coastal bed-and-breakfast, you won’t be disappointed by your options. Brass Lantern Inn is a classic-yet-modern bed and breakfast in the Cultural Historic District. The Seven Sea Street Inn, another true bed and breakfast experience, has been in business since its conception by its innkeepers in 1987. Plus, both inns happen to be just a walk away from Historic Main Street where Christmas Stroll entertainment will take place.

For travelers with more of a hankering for a hotel stay, the Blue Iris might just do the trick. As one of luxury hotel brand Life House’s newer hotels, the Blue Iris offers a tasteful balance between eclectic charm and lavish amenities, so it always feels like home away from home. Faraway hotel is another sure way to maximize your winter Nantucket trip. Faraway’s eclectic-yet-cozy interior and welcoming feel will be the inspiration you need to get ready for the Nantucket-style celebrations to come.

/ Bill Hoenk Photography

Where to Eat During Your Stay

Nantucket has hundreds of local businesses that are serving both fantastic food and good times. For those who are familiar with the Island’s nightlife, The Rose & Crown may come to mind. This iconic establishment is an excellent choice for a family-friendly sit-down dinner, as well as a night out at the local bar to top off a day of Christmas Stroll festivities. The Rose & Crown often has live music and DJs after 10 p.m., so stay tuned for their schedule of happenings.

Fueling up for each day’s events will be essential to making the most out of the weekend. Island Kitchen is a great place to start your day with a nutritious and flavorful breakfast.

Another top-rated place to eat, or, The Whale, is an upscale concept right on Main Street whose namesake is inspired by Herman Mellville’s “Moby Dick,” which famously pays homage to the island of Nantucket. or, The Whale’s inventive-yet-approachable menu will offer just the warmth you need after a day spent outside in the crisp Nantucket air, with entrees for one and tempting shareable plates for two to six people.

Christmas Stroll visitors love the island’s snow-dusted scenery and quiet serenity, which has its own appeal compared to the busy summer season. Across the island, you will find the best holiday sights, sounds, and flavors that you won’t find anywhere else.


To learn more, visit nantucketchamber.org/christmas-stroll