Chesapeake Bay Bridge
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Travel Around the Great Chesapeake Bay Loop

Chesapeake Bay Bridge
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The elegant, dual spans of Maryland’s Chesapeake Bay Bridge that cross the wide waters of the middle Chesapeake, and the engineering marvel that is the Chesapeake Bay Bridge Tunnel at its mouth open the bay to road tripping adventures. You can circumnavigate the Chesapeake in one big loop; just do the Upper Bay Loop or Lower Bay Loop; or a fun figure-8 crisscrossing America’s largest estuary.

BaltimoreAnnapolisGalesvilleChesapeake BeachSolomonsLeonardtownSt. Mary's CityCrisfieldCambridgeEastonSt. MichaelsKent NarrowsRock HallChestertownChesapeake CityNorth EastHavre de Grace

However you decide to travel around the Chesapeake be sure to utilize Maryland’s scenic byways for the most enjoyable route. Follow as little, or as much, of a scenic byway as you want.  Also check out Maryland's complete list of Scenic Byways.

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Quintessential Chesapeake Bay Towns

25 Can't Miss Things to do Along the Great Chesapeake Bay Loop

Stay Along the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop


Chesapeake Country
Chesapeake City

It is said that life in "Chesapeake Country" flows gently with the tide of North America's largest estuary and its tributaries. Take your time experiencing the special beauty of this tidewater region with its pristine waterways and vibrant historic waterfront villages.

Harriet Tubman Underground Railroad
sculpture of Harriet Tubman
Chiodo Art

The sculpture Unwavering Courage in the Pursuit of Freedom in Tubman Garrett Park, Wilmington, Delaware. Photo Credit: Chiodo Art

Explore the secret network of trails, waterways and safe houses used by enslaves people fleeing north to escape slavery. 

John Wilkes Booth: Chasing Lincoln’s Assassin
John Wilkes Booth

Follow the escape route of John Wilkes Booth, one of history’s most notorious assassins, as he fled from Washington, D.C,. and hid for several days in Southern Maryland before being cornered. 


Religious Freedom
stained glass window

America’s roots of religious tolerance run deep in Southern Maryland, where some of the nation’s oldest churches are an indelible part of this peaceful, small-town landscape.

Star-Spangled Banner
Learn about the War of 1812 here where the flag that inspired the National Anthem was sewn.

Follow the trail of British troops as they fought their way up the Chesapeake Bay during the War of 1812, eventually clashing with American defenders in a battle immortalized by the “Star-Spangled Banner.”

Roots and Tides
Enjoy the hands-on exhibits and overnight programs at the lighthouse at this museum.

Discover the heritage of oystering and crabbing at the Chesapeake Bay Maritime Museum. The museum displays a large collection of working and recreational watercraft and hosts exhibits on bay history and waterfowl hunting.

Explore the timeless traditions and deep maritime roots of Western Shore towns along the Chesapeake Bay. Go sailing, bird watching, museum hopping or just relax on a sandy beach.

Lower Susquehanna
Red Loch house

For anyone interested in maritime history, fishing, shopping or sweeping river views, this unhurried drive offers plenty of opportunities to stop and explore.

Map of the the Great Chesapeake Bay Loop

See map of the the Great Chesapeake Bay Loop.
View Image.
View pdf.