7 Best Shopping in Boston, Massachusetts

A throwback to another era, this storied museum-like tobacco shop has been in the same location since 1883, when it served as a clubby gathering spot for young Harvard men, who puffed away while playing pool on the back billiard tables. While Harvard oars, hockey sticks, and photos still adorn the ivy-green walls, the store now caters to a broader clientele in search of quality smoking items, old-fashioned straight razors and shave brushes, chess and checker sets, and small gift items, such as beer steins.

If you've shopped Charles Street in the last 45 years, you'll recognize this long-standing shop, now in a much larger location. Many of the gifts, books, and greeting cards on display are made in the United States and locally focused. The back room boasts an awesome selection of spices, Swedish dish cloths, and small kitchen utensils.

Look for the lifelike golden retriever that guards the entrance to this shop named for its location at the base—or, flat—of Beacon Hill. The semi-preppy selection includes loads of candles, unique jewelry, hand-woven totes from Mexico, and a well-curated range of fancy souvenirs like Boston University winter hats and embroidered canvas Massachusetts travel bags.

Enchanting homemade gifts from a rotating group of more than 60 artists (including the owner, Marie Corcoran) fill this dreamy boutique. Scoop up dainty charm and gemstone pendants, vegan handbags, men's handpainted ties, or a cute caterpillar wooden wall clock for that special little one in your life. This store has something for everyone, including you.

This home and boutique shop is the perfect stop along the Freedom Trail for gifts galore. Treat yourself to home accents like candles and vases, or channel a little New England with items such as lobster trays, oyster salad plates, and pizza peels decorated with Charlestown typography. The shelves are also stocked with fashion-forward items like bracelets, rings, and headbands for an accessory shopping spree.