Travel Around the Great Chesapeake Bay Loop



Featured Places

Chesapeake Bay Bridge
Chesapeake Bay Bridge at Twilight
Image Credit: @Motoxdms - Instagram

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

Experiences Along the Great Chesapeake Bay Loop

Stay Along the Great Chesapeake Bay Loop

Trip Suggestions for the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

Chesapeake City Image Credit:

Chesapeake Country

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.

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sculpture of Harriet Tubman Image Credit: Chiodo Art

Harriet Tubman Underground Railroad

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

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John Wilkes Booth

Booth’s Escape

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.

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stained glass window

Religious Freedom

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.

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

Star-Spangled Banner

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.”

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

Roots and Tides

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.

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Red Loch house

Lower Susquehanna

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

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Map of the the Great Chesapeake Bay Loop

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


About Authentic

Experiences Along the Great Chesapeake Bay Loop


People on a boat crossing the bay to St. Michaels
Trip Suggestions for the Great Chesapeake Bay Loop

With the Great Chesapeake Bay Loop the miles of adventure are unlimited. Explore for a day, escape for a long weekend, or spend a vacation week, or more, enjoying all there is...


Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
Touring the Islands of Maryland

Want to get away to the islands? Maryland is home to hundreds of islands just waiting to be explored! Some are uninhabited or strictly nature preserves, while others are...


Sunrise at the Susquehanna River Bridge in Havre de Grace
Quintessential Chesapeake Bay Towns



Carroll Wine Trail
Breweries, Wineries and Distilleries

Search our list of Maryland breweries, wineries and distilleries here.


Visit the national park famous for its horses that roam free.
15 Epic Ways to Experience Authentic Maryland

Famous local dishes, one-of-a-kind landmarks and unique cities and towns: these 15 only-in-Maryland experiences will spark your imagination.