Main Street, Annapolis (must see)

Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks, views of the Annapolis Harbor, and bustling shops. They say that Main Street is the lifeblood of Annapolis and, indeed, represents the very best of what the state of Maryland has to offer. Defined by as much as three centuries of history and lovingly-preserved 18th- and 19th-century buildings lining its five blocks, this thoroughfare is something of a living museum, providing visitors and residents alike with some truly historical experience.

Given the assembly of architectural details, attractive qualities, interesting discoveries, and everyday pleasures found here, it is easy to see why Main Street is a source of pride not only for Annapolitans, but for Americans across the country. Nightlife, dining, and art, as well as shopping take the center stage here, making Main Street a great point to start a day on the town, be it for a leisurely outing, special event, or some other occasion.

There's a contagious energy in the air of Main Street that some call addictive. Just look in any direction and you will surely find something to pique your imagination - physically and visually associated with history, maritime culture, and architectural character. Among the eye catchers are, undoubtedly, the Chesapeake Bay, midshipmen in dress whites, historic landmarks, bars, restaurants and art galleries of every size and description, offering visitors plenty of options to choose from, no matter what they look for. There are also a handful of cafes, ice cream parlors, bookstores, and shops selling souvenirs, jewelry, comics, and apparel aimed at tourists to be found.

Throughout the year, the city and merchants decorate the street with hanging flower baskets, flags, and banners. Each October brings visitors in their thousands who arrive for the world's largest in-water power and sail boat shows taking place at City Dock. The street has a festive atmosphere during the holiday season too, when the Downtown Business Association and businesses along Main Street sponsor Midnight Madness two nights before Christmas to attract holiday shoppers to their decorated stores.