Annapolis may be referred to as the “Sailing Capital of the U.S.” and known for its history, but did you know it is a shopper’s paradise? Here in Annapolis, you can find an array of shops that fit everyone’s styles. From eclectic boutique shops to quaint bookstores, and antique treasures to art galleries, you’ll find it here. If you’re looking for that special one-stop-shop to experience all Annapolis has to offer, there’s no better place to go than the Annapolis Boutique District, also known as Maryland Avenue.

Annapolis Boutique District

With over twenty small specialty stores making up Maryland Avenue, it’s worth finding time to discover this modern, yet historical shopping experience. Plus, the street is also home to amazing restaurants that can take care of that appetite you just built up. Keep heading down Maryland Avenue and you’ll end up at Gate 3 of the United States Naval Academy, steps away from the world-class USNA Museum and the perfect starting point for a walk around the “Yard” – a must for any military history buff.

I promise, you won’t be disappointed!


Videography and photos courtesy of Patrick McNamara of Drawn to the Image.

Kat Spitzer

Kat Spitzer is the author of The Happy Hypochondriac and The Happy Hypochondriac Survives World Travel. She also writes the Happy Hypochondriac humor blog at She is a columnist and freelancer for various newspapers and magazines, and is currently working on her third book. Kat is also the owner and instructor of Miss Dawson’s School for Well-Mannered Individuals, an etiquette program in Annapolis ( She graduated from Vanderbilt University and Vermont Law School, and lives in Annapolis with her husband and two children.