Explore Historic Annapolis on Foot

Stroll through centuries of history on a self-guided walking tour of downtown Annapolis, Maryland, a Chesapeake Gateways Network Experience. Much like Boston’s Freedom Trail, this route weaves together significant places that tell the city’s story as a center of political, cultural, and maritime life along the Chesapeake Bay. The walk begins at City Dock, where waterborne commerce once connected Annapolis to the wider Bay and beyond. From there, the route leads to notable sites such as the Maryland State House, where the Continental Congress met, and the U.S. Naval Academy’s historic John Barry Gate, linking the city to the nation’s maritime legacy. Along the way, visitors encounter homes of free and enslaved African Americans, including the Butler and Maynard Burgess Houses, as well as landmarks of faith and community such as St. Anne’s Church and Asbury United Methodist Church. The Banneker-Douglass-Tubman Museum highlights the enduring story of African American heritage and activism in the Chesapeake region. The walking tour can be followed at your own pace using your mobile device and the NPS App, guiding you through Annapolis’s streets, churches, gardens, and public squares that reflect the diverse stories of the people who shaped the city and the Bay. The tour itself is free, though some museums and buildings may require admission when open. To learn more, explore the App or visit the Chesapeake Gateways website.