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Take a Day Trip to the Colonial Annapolis Historic District

colonial Annapolis historic district

Main Street is a great place to start exploring the colonial Annapolis historic district.


Baltimore and Washington DC are convenient to the Wayside Inn in historic Ellicott City, but a charming and equally historic site nearby is the colonial Annapolis historic district. We believe that this Maryland coastal town is one of the best places to visit on the American East Coast.

Curious to find out why? Read on!

For our recommendations on what to see and do in Howard County, download our free area vacation guide.

Annapolis was a colonial capital city known as the Athens of America. As a seaport, Annapolis was a cosmopolitan hub. Now, you can experience the contemporary appeal of the colonial Annapolis historic district with all the wonder of American history at the same time.

Colonial Annapolis Historic District

Designed in the European fashion, the layout of Annapolis is a constant reminder of its historic past. St. Anne’s Episcopal Church and the State House are focal points of the circular, radiating streets. The design was so admired by frequent visitor George Washington that he incorporated it into the design of the nation’s capital. The Maryland State House, the oldest such capital building in continuous use in the United States. Annapolis also featured the first theater in the new world.

Today, Annapolis has more of these original 18th-century structures standing than any other city in the United States. You can certainly stroll by them and admire them from outside in this very walkable city, but many are open to the public.

Today, the Maryland Hall for the Creative Arts is a thriving center for studying, exhibiting, performing, and practicing the arts. Resident companies include the ballet, symphony, opera, and chorale.

United States Naval Academy

The most widely known site in the colonial Annapolis historic district is, of course, the U.S. Naval Academy. But Annapolis is also home to another historic college: St. John’s College, founded in 1696, the third oldest college in the United States (after Harvard and William and Mary).

Annapolis and the Chesapeake

The same Tidewater cuisine which was appreciated in our colonial period is still a major part of Annapolis. The town’s many excellent pubs and restaurants offer Maryland specialties from the Chesapeake Bay. Some even date back to the 18th century. As in colonial Annapolis, music is a part of the ambiance, and almost any night of the week you can find live entertainment in a number of venues.

Annapolis is a very popular port of call for international sailors. An annual Maritime Heritage festival is held on the City Dock to celebrate this aspect of the Annapolis lifestyle. In the fall, the largest in the water boat shows in the world are held on successive weekends for sail and power enthusiasts.

Exploring Colonial Annapolis Historic District

The Capital City Colonials Tours offer a number of excellent options for walking and riding tours with colonial-dressed guides:

Annapolis-in-an-Hour, Annapolis Food & History Tour, Historic District 101, Women of Annapolis, Washington’s Resignation, The Jonas Green House, The Sands’ House, Colonial Gossip, and Grand Houses

You can also enjoy the U.S. Naval Academy on foot with its guided talking tours. For more information go to the Academy’s visitors web page.


We’d love to be your home base for all of your Howard County adventures here at the historic Wayside Inn. Our free Howard County vacation guide can help you plan your trip!