Nantucket conjures a specific set of images: lobster rolls, lighthouses, navy crewneck sweaters and soft island-sand beaches. It’s a quintessential New England summer destination, heavily populated by those in a high tax bracket. But in December, Nantucket transforms into an egalitarian winter wonderland focused on supporting small businesses and celebrating the holiday season.
Christmas Stroll, hosted on island the first weekend of December every year, has become a hallmark Nantucket event. The tradition began in 1973 when shop owners stayed open late to encourage locals to do their holiday shopping locally rather than ferrying over to Cape Cod to purchase gifts. Since then, it’s become quite a bit more than extended store hours.
PHOTO: CELINA COLBY
The weekend-long contemporary edition of the festival features dozens of holiday trees lining streets in the downtown area, culminating in a 20-foot tree at the entrance to Main Street. Shops participate in a storefront-decorating contest, competing for the wholesome honor of bringer of the most holiday cheer.
Another element that’s evolved since the launch of Stroll is the increased number of Black and other BIPOC-owned businesses on the island. Local artist Avereon Evering creates handmade items from rescued materials, like a decoupage shell wreath that blends Nantucket’s nautical history with the holiday season. At The Green Lady Dispensary, the first women- and minority-owned cannabis company in Massachusetts, the Campbell family curates herbal gifts rooted in their Jamaican heritage. Skin care mavens Bianca Blahnik and Shantaw Bloise-Murphy craft body butters, lotions and candles in a low-waste process for their beauty brand Supple Sirens.
After exploring the shops and fulfilling a few holiday wish lists, fuel up at or, The Whale, a chic restaurant where chef Manny Rojas infuses the menu with Mexican and Caribbean influences. Or, go more casual and grab a piping hot plate of Salvadoran pupusas at Nantucket Trading Post.
PHOTO: CELINA COLBY
During Christmas Stroll, visitors hear carolers walking the streets, watch a full program of performances at the live entertainment stage and sample holiday treats passed out by local businesses. Four Winds Gifts, Nantucket’s oldest gift shop, distributed steaming cups of hot chocolate to shoppers this year. Shops even create branded merchandise celebrating the festival each year. Santa is in attendance and, in true islander fashion, he arrives by boat.
Though Stroll has become a Nantucket phenomenon, it’s not the only way to experience holiday festivities off the Massachusetts mainland. Nantucket is just as magical the rest of December, and significantly less crowded.
The Nantucket Hotel, the inspiration for Elin Hilderbrand’s similarly titled novel, “The Hotel Nantucket,” is a convenient base camp for a winter adventure on island. Located within quick walking distance to downtown, the property also features cozy and convenient amenities onsite, like outdoor fire pits and a full-service spa and fitness club to which guests have automatic access.
PHOTO: CELINA COLBY
From there, it’s an easy walk to notable island sites like the Whaling Museum and the Brant Point Lighthouse, decorated for the holidays by floral installation designer Hafsa Lewis.
Venture out of the immediate downtown area to visit the Nantucket location of the Museum of African American History. The museum owns a number of sites on the island, including a 19th-century African Meeting House and the home of 18th-century weaver Seneca Boston. The museum is a convenient starting point to walk the Black Heritage Trail on Nantucket, visiting 10 stops connected to the diverse history of the island.
After Stroll, the crowds die down, but the restaurants and attractions on Nantucket remain lively through the holidays. For travelers who don’t mind a little nip in the air — and let’s be honest, Bostonians are used to that — December is the ideal time to visit the otherwise crowded and pricey vacation spot. Twinkling lights and festive holiday activities fill the December calendar and you can still have all the lobster your heart desires.
