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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.


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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 location in which visitors can shop, eat, and soak up the ambience. Many residents live nearby, creating the need for a variety of goods and services here. Special events and activities are held throughout the year, adding to the district's appeal. Retail merchandise runs the gamut, from clothing to sports gear, jewelry, to toys. The holidays see the area really come to life with decorations hung throughout the streets and in the stores, and a pop up marketplace that specializes in local artisan goods. A number of fine dining venues, nightclubs, and theaters also call Downtown Crossing home.

Recommended for Christmas Shopping because: The Downtown Crossing Holiday Marketplace adds to the already bustling shopping scene; you'll find a selection of locally crafted gifts.

Jessica's expert tip: Holiday shopping is best at the Downtown Crossing Holiday Marketplace.

Read more about Downtown Crossing →




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 away from Boston, Wrentham Village Premium Outlets is worth the drive to buy the Kate Spade clutch you've been eyeing or the Brooks Brothers suit you've been dying to buy. Beyond attire, the Wrentham Outlets has many retailers selling housewares, and food items. Add to that a walkable outdoor landscape and you can enjoy the outdoors while getting your shopping fix. Like any shopping in Massachusetts, all clothing purchases are made tax free.

Recommended for Christmas Shopping because: Bargain hunters looking for designer labels will find big name items at an excellent discount the Wrentham Village Premium Outlets.

Jessica's expert tip: AAA members receive free coupon books at guest services (but others can purchase a book for a small fee) as well as discounts in many stores just by showing your card. Ask in every outlet store to see just how deep a discount you can get.

Read more about Wrentham Village Premium Outlets →


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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 popping in and out of popular shops, and boutique featuring local goods and familiar brands. You'll find holiday gifts for everyone on your list, and most picks will be a bit different than what you'll find at the local mall; ensuring you're gift will be extra special. Enjoy the beauty treatments available and then make your way to one of the restaurants for a bite. After your done, or in place of a restaurant meal, take a break by buying tickets at the upscale cinema and catch a movie while you dine with in seat service before packing up your purchases and heading home.

Recommended for Christmas Shopping because: Specialty stores packed with unique find and lots of activities to entertain the family while you shop makes The Street ideal for Christmas shopping.

Jessica's expert tip: Check the calendar for special attractions and discounts happening regularly at The Street

Read more about The Street →


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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 architecture has been updated from the run of the mill to a spectacularly serene setting. With more than 7,000 parking spaces, including valet and premium parking, Natick Mall offers more FREE parking options than any surrounding retail destination to ensure your bags find their way home with ease. Located just twenty minutes west of Boston, you can easily breeze to the Natick Mall and make it back to the city before dinner.

Recommended for Christmas Shopping because: At the Natick Mall you'll find the best Santa for photo opportunities, gorgeous decor and every store you'll need to do it all in one spot.

Jessica's expert tip: Check the mall website for special event. For instance, every Tuesday Pottery Barn kids holds story-time, Williams Sonoma offers cooking classes, and Metrowest Stroller Strides holds fitness classes here when the weather outside is not up to par.

Read more about Natick Mall →


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 has a pleasant food court where shoppers can grab a quick bite between stores. And for those seeking a more relaxing dining experience various restaurants call the Prudential Center Home including Legal Seafood, and the Cheesecake Factory. Connected copley Place, the Sheraton and Mandarin Oriental you can cover a great deal of the Back Bay without leaving this enclosed space. For truly great views, the Prudential Tower's Skywalk Observatory offers an unparalleled perspective of the city and beyond.

Recommended for Christmas Shopping because: The atrium style of the Shops at the Prudential Center gives you the feel of shopping outdoors while staying warm.

Jessica's expert tip: The indoor structure is connected to Copley Place, be sure to make your way across the bridge for even more shopping.

Read more about The Shops at Prudential Center →


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 epicenter of Boston's shopping district. Surrounded by fashionable stores that run the gamete from high end to main stream,you can do all of your holiday shopping in the area; that is if you come out of Craft Boston without the ideal gift for everyone on your list. Craft Boston is special; here you'll be able to shop for unique, one-of-a-kind gifts, meet the makers you are supporting, and learn about fine contemporary craft. Craft Boston offers you a way to buy local beyond food.

Recommended for Christmas Shopping because: CraftBoston Holiday is different experience, where you'll find one of a kind hand made gifts from local artisans.

Jessica's expert tip: Best for those looking for fun, funky finds in the are of housewares, jewelry or other specialty items.

Read more about CraftBoston Holiday →




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 Washington, which earned it the nickname "Cradle of Liberty." In the 1970s, a major renovation to the aging structure transformed it into one of America's premiere urban marketplaces. Now, it boasts more than 50 shops, 14 restaurants, and 40 food stalls. Some folks (and publications) refer to the retail component as Quincy Market. Here you'll be able to pop in and out of stores while enjoying a piece of the Freedom Trail.

Recommended for Christmas Shopping because: Holiday lights, festive music and Boston based gifts will put you in the spirit of the holidays at Faneuil Hall Marketplace.

Jessica's expert tip: Many retailers here cannot be found elsewhere like the Boston Sports Store geared towards ladies, Lucy's League.

Read more about Faneuil Hall Marketplace →




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 mavens: hip and cutting edge, to classic and trendy. If you're looking for an original gift for those on your list you'll be sure to find something at Sowa. The array of indie goods available range from handbags, jewelry, pottery, letterpress stationery, silk-screened t-shirts, baby clothes, and even re-purposed wool accessories. Held off-site of the main Sowa marketplace, this holiday shoping extravaganza is one weekend only (december 14 & 15, 2013) and is in the historic main building of the Benjamin Franklin Institute in Boston's South End. If you happen to miss the market, make your way to Sowa's "home" on Harrison Ave on Sundays and shop in the indoor vintage market.

Recommended for Christmas Shopping because: The Sowa Holiday Market is a Boston tradition where you'll find the best local goods around-ideal for giving!

Jessica's expert tip: One weekend only, this can't miss shopping experience may fill all your holiday buying needs, bring cash as some vendors prefer that method over credit.

Read more about SoWa Open Market →


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 New York's Fifth Avenue, or California's Rodeo Drive. Shopping starts at Massachusetts Avenue and continues to Arlington Street, spanning a mere eight city blocks. The historic storefronts offer charming glimpses of Boston during the mid-to-late 19th century. Open air cafes and restaurants can be found lining the sidewalks and offer the perfect place for people watching when you tire of shopping.

Recommended for Christmas Shopping because: Nothing says holiday shopping like Newbury Street where the fresh air and variety of stores brings Christmas to life.

Jessica's expert tip: Begin at Mass Ave and make your way to Arlington Street, the closer you get to Arlington the pricier the stores you encounter.

Read more about Newbury Street →


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 decision making difficult but those you buy for quite happy. You may just be able to get your shopping done before Thanksgiving. Aside from getting your shopping done, you'll be treated to a creative art display of gingerbread houses. The auctioned off edible creations are judged each year, prior to the opening of the Christmas Festival, by local media and their children. Awarding the area chefs who donated their time, hard work and competitive spirit to raise money for Housing Families, bragging rights.

Recommended for Christmas Shopping because: The Christmas Festival and Gingerbread House Competition is the ideal place to find something special for your someone special.

Jessica's expert tip: Held the first weekend in November, this craft festival is well worth putting in your calendar.

Read more about Christmas Festival and Gingerbread House Competition →


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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. 

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