Where is the best shopping in Annapolis?

Answers from Our Experts (1)

Hayley Bosch

Over the past 10 years, Annapolis’s shopping options have grown with the introduction of several upscale shopping areas and further development of the historic area. Forbes Travel Guide editors suggest starting on Main Street, which bustles with boutique shopping ranging from Helly Hansen (top-notch sailing gear) to Laurance Clothing (classic preppy menswear). There are a slew of good souvenir shops downtown, including Pepper’s and A.L. Goodies General Store. West Street, in Annapolis’ up-and-coming Uptown neighborhood, has its own share of boutiques and restaurants.
 
The Parole neighborhood’s Westfield Annapolis Shopping Mall has department stores like Macy’s and Nordstrom, as well as specialty spots like the Apple Store and Sony. You’ll also find the Under Armour store — it is a Maryland company after all — and a movie theater. Across the way is the city’s most recent addition, Annapolis Towne Centre at Parole. Here you’ll find hip shops like Lululemon Athletica, Anthropologie and boutiques like Urban Chic.

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