Annapolis Walking Tour: Where History Meets the Water

Annapolis has been shaped by the water at its doorstep for nearly four centuries. On this walking tour, you'll trace how the Chesapeake Bay turned a small colonial settlement into a hub of revolutionary history, maritime culture along with U.S. Navy influence, and African American heritage.

The tour starts outside the Museum of Historic Annapolis on Main Street. You'll walk toward the harbour at Ego Alley, where locals still navigate their boats in slow, deliberate loops for admiring crowds, then wind through Pinkney Street's 18th-century wooden homes before heading toward the grand brick mansions of Prince George Street and Maryland Avenue. Along the way, you'll hear how tobacco wealth, enslaved labour, and the ambitions of Maryland's planter class built this city from the waterfront up.

You'll discover how George Washington's resignation as Commander-in-Chief in the Maryland State House – the oldest still in legislative use in the country – stunned governments worldwide. You'll also learn how the Treaty of Paris was ratified in this same building, officially ending the Revolutionary War. The tour ends back on Main Street, where a bar still bears the sign that John Adams, John Jay, and Benjamin Franklin drank here.

On this 60-minute tour, you'll have a chance to:

• See the Kunte Kinte Memorial, the only U.S. site commemorating the name and arrival of an enslaved African
• Admire the Hammond-Harwood House's front door, which Thomas Jefferson called the most beautiful in America
• Learn how a dovecote, a header brick bond, and a boat in Ego Alley all signalled the same thing: wealth
• View the wide variety of homes in this small town, from wooden labours' homes to grand mansions owned by signers of the Declaration of Independence
• Visit Lawyers' Mall and its statue of Thurgood Marshall, who argued landmark civil rights cases before the Supreme Court
• Explore the Banneker-Douglass-Tubman Museum, chronicling African American life in colonial Maryland

The tour ends as you walk down Main Street toward the starting point and water so you can revisit any stops or check out new places.

Annapolis rewards slow exploration, so take your time, duck into a tavern, and stay for the oysters and crab cakes.