Shopping in Annapolis falls into 4 distinct areas...

area 1 Main Street is where you will find all the shops for souviniers, t-shirts etc,

area 2 is Maryland Ave and State Circle where you find interior decorator shops and antiques stores,

area 3 is West street a new upcoming street starting fill up with art galleries, upscale shopping and dining,

area 4 is just outside of down with all the chain stores and shopping malls. The nice thing about shopping in downtown Annapolis is the lack of chain stores. The town also has a lot of fine art and craft galleries all in walking distance of each other.  There is also an outdoor art market held on the first block of West street on the First Sunday of each month (May-October) that is alot of fun to shop at.