Boston Christmas Shopping: The Best Streets, Malls, Centers and Craft Fairs

Boston's four seasons add to the ambiance of holiday shopping. As the temperatures drop, Bostonians bundle up in cozy sweaters, snug socks, and down jackets, ready to enjoy the crisp fresh air of the winter season and the joy of Christmas shopping in a city that feels like Christmas.  Whether Christmas shopping indoors or out, Boston stores will wow the Scrooge out of even the toughest customer.

Find everything you need for everyone on your list while strolling the streets of Boston where popular shopping destinations transform into winter wonderlands where you'll not only make your purchases but also enjoy the extensive decor, displays and possibly even a touch of snow along the way. 

With special "holiday only" shopping at spots like the weekend long Sowa Holiday Market and the tented, seasonal Downtown Crossing Holiday Marketplace you can find a variety of hand crafted specialty items that are sure to be big hits with those on your list.

Four season favorite shopping spots fall into the Christmas spirit. You'll find decor heavy stores, malls and marketplaces that will have you wishing you weren't too old to sit on Santa's lap. Enjoy the fresh air with a cup of something hot while strolling the shops at Faneuil Hall Marketplace or seeking deep discounts on designer duds for the label lover on your list at the Wrentham Village Premium Outlets. Or stay warm at indoor malls like the atrium covered Prudential Center.



Downtown Crossing is an Boston area that is going through major changes. Parking lots are being transformed into multi-use buildings creating more need for shopping in an area that already specializes in just that. This area offers a centralized...  Read More



Wrentham Village Premium Outlets was built with bargain hunters in mind. Wrentham Village Premium Outlet Center is home to one hundred and seventy high end retail outlets, all offering reduced pricing on their premium goods. Less than an hour...  Read More

West Metro


The Street in Chestnut Hill is an upscale lifestyle center ideal for shopping, dining and finding some entertainment. Seasonal specials add a bit of entertainment to this lifestyle center that mimics the feel of a main street. Enjoy the day...  Read More



The Natick Mall is the largest mall around. Home to two hundred retail stores, the Natick Mall is anchored by lavish retailers like Neiman Marcus and Nordstrom as well as affordable stores such as JC Penney and Sears. The Natick Mall's indoor...  Read More

The Shops at Prudential Center
Photo courtesy of Wrentham Village Premium Outlets/Facebook


Billed as one of the Northeast's top shopping destinations, the exclusive Prudential Center offers well over 75 retail establishments, including Barnes & Noble, Saks Fifth Avenue, Lacoste, Lord & Taylor, and Club Monaco. The mall also...  Read More

CraftBoston Holiday
Photo courtesy of CraftBoston


Enjoy a little something special at CraftBoston Holiday. This highly regarded event is a must-attend for artists, collectors, and craft enthusiasts. Held in the spacious Hynes Convention Center in bustling Back Bay, CraftBoston Holiday is in the...  Read More



A Boston social and commercial centerpiece since 1742, Faneuil Hall was originally established as a market for merchants, fishermen and vendors. It later hosted inspirational appearances by prominent figures like Samuel Adams and George...  Read More



An annual Boston tradition, the Sowa Holiday Market lets you shop the very best goods offered from New England's independent producers including designers, artists and crafters. You'll find chic fashions that appeal to a variety of style...  Read More

Newbury Street


Newbury Street shopping has everything from fun and funky finds at stores like the hip chain Urban Outfitters to the classic couture that is offered at Chanel. Plus everything in between. Newbury Street is known as a high end shopping spot like...  Read More

Christmas Festival and Gingerbread House Competition
Photo courtesy of Jessica Polizzotti


Enjoy a day of shopping the unique crafts, food and artistry of the more than 350 vendors at this annual holiday market. With a variety of options to choose from, you'll find yourself overwhelmed by the truly special gifts you will find, making...  Read More


Meet Jessica Polizzotti

Born and raised in Boston, Jessica knows her city like the back of her hand.  Always looking to uncover something new, Jessica keeps up on the latest and greatest Boston offerings. 

Although...  More About Jessica