Pit Stops
The Annapolis Bookstore
Stop by the Maryland Avenue favorite and enjoy a nice cup of coffee and a classic read on their terrace. Like walking through someone’s home filled to the brim with books, this local shop is homey and welcoming. 35 Maryland Ave.
Annapolis Ice Cream Company
There are plenty of places to grab a cone on Main Street, but this local shop is said to be the best. Their ice cream is made right at the store every day, so it’s the perfect spot to grab a fresh scoop. 196 Main St.
Federal House Bar & Grille
Finish your trip with a drink and some local fare like crab soup or crab cakes at this dock-front bar. With outdoor seating near the water, this is a great place to end your relaxing shopping day. 22 Market Pl.