Things To Do

There’s a wide variety of things to do, see, and learn about in the Chesapeake Crossroads Heritage Area. From historic, 18th-century architecture and the United States Naval Academy in the city of Annapolis, to the beauty of the Chesapeake Bay and the area’s art and culture, there’s a little something for everyone. Below is a quick list of of things to do, see, and experience the next time you’re in the heritage area. Start planning your trip today!

The confluence of the Chesapeake Bay to the east and the area’s numerous creeks and rivers defined the area’s natural and man-made landscape and shaped the lives of those who settled along its shores.

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Annapolis enjoyed what’s been called its “golden age” from the late 1750s to 1776.  At the time, the town was described by Jonathan Boucher, rector of St. Anne’s Church in 1772, as the “genteelest town in North America.”


It’s as though the city was built as an extensive, outdoor gallery—or, as Historic Annapolis designated it over fifty years ago, as “a museum without walls.”

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Annapolis’s historic fabric remains remarkably intact, thanks in large part to historic preservation efforts that began as early as the 1880s.


Anne Arundel County owes much to the rich heritage, culture, and bravery shown by African-American Marylanders. Their labor was the backbone that built the strong local economy and the beginning of America’s early infrastructure.

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Formal training for naval officers began in 1845 when, under the direction of Secretary of the Navy George Bancroft, the Naval School was established in Annapolis in October 1845, with a class of fifty midshipmen and seven professors.


Recreational Trails

Getting outdoors is one of the best ways to explore and appreciate all our area has to offer. Bike, hike, or walk the recreational trails of Anne Arundel County and discover something new through these outdoor experiences.

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Explore New Sites

The Chesapeake Crossroads Heritage Area has had a recent Boundary Expansion, and new sites, museums, parks, trails and more — are now included among our partners. This page will help you explore new places and plan new experiences.


Four Rivers Heritage in Annapolis and the Chesapeake Bay