Are you a spontaneous shopper? If so, you’ll love downtown Annapolis. In this historic, walkable town, you don’t have to make a special trip to go shopping. Say you’re in Annapolis having lunch with friends or the family, or spending the afternoon sailing. Or perhaps you came to tour historic giants like the Naval Academy or the Maryland State House.

Whatever your agenda, in downtown Annapolis you’re never far from great one-of-a-kind shops and boutiques. You’ll find plenty of shopping on Main and West Streets—but don’t count out shops that may be tucked away on streets that take you slightly off the main drag. 

History, Shopping, Dining on Maryland Ave

Maryland Avenue is a perfect example of the out-of-sight—but not out-of-the-way—streets in Annapolis where you’ll find hidden shopping hubs. In the shadow of the Maryland State House, the quaint and windy street in downtown Annapolis offers visitors an unparalleled shopping experience. And it’s been doing so for quite some time. 

Maryland Avenue fall Festival

With the inception of the United States Naval Academy in 1845, the far end of Maryland Avenue became the main entrance to the school. Today, this entrance provides quick access to the USNA Museum, Bancroft Hall, and the Naval Academy Chapel. Since the establishment of the Naval Academy, Maryland Avenue has supplied the school, local residents, and visitors with a living history of American shop-keeping. For more than a century, its proud local and devoted businesses have stood out as one of the last mainstays of small, historic, independent specialty shops in Maryland.

Maryland Ave's history

Before Maryland Avenue became a commercial hub, it was the most fashionable residential street in the area, housing wealthy statesmen and land owners like Matthias Hammond (Hammond-Harwood House, 19 Maryland Avenue) and Samuel Chase (Chase-Lloyd House, 22 Maryland Avenue). Hailed as some of the most important examples of colonial architecture in the country, these homes still stand and are open for public viewing. Through the centuries, they’ve stood alongside independently owned stores. 


You may be wondering what kinds of shops you’ll find on Maryland Avenue today. The answer is a little bit of everything, really. There’s a book store that’s perfect for leisurely poking; there, you’ll find new, used, and rare books in a quiet setting complete with large, comfortable reading chairs and a small café

Shops on Maryland Avenue

If antique stores speak to you, you’ll find two on Maryland Avenue. Among the unique treasures, you might discover a centuries-old relic from Annapolis or the Chesapeake Bay region. Are you a gourmet food lover? You’ll enjoy upscale foods, beer, wine, gifts, and gift baskets of all shapes and sizes at a store that’s a favorite with tourists and locals. There are also upscale women’s and children’s clothing stores, gift shops, an art gallery and even a barber shop on Maryland Avenue. 

With over twenty small specialty stores lining Maryland Avenue, it’s worth finding the time between other pursuits in Annapolis to nose around the shops here. You may even want to plan your trip to Annapolis around this picturesque, old-fashioned (and high-fashion!) center of commercial activity.

Come to Maryland Avenue and experience a thoroughly modern—and historical—shopping experience. See below for a full list of things to do and local businesses that call Maryland Avenue home.