Great Chesapeake Bay Loop



Enjoy a crab feast at the Crab Claw in St. Michaels.
Crabs at Crab Claw in St. Michaels
Photo By: Clark Vandergrift
With rides and amusements open 'til the wee hours, O.C. is a nightlife hotspot.
Ocean City Amusements at Night
Photo By: Clark Vandergrift

Heaven and earth never agreed better to frame a place for man’s habitation. ~ Captain John Smith, English Explorer, 1609.

Framed by sandy shores, shaded by lush forests and marshes, and dotted with waterfront cities and towns, the Chesapeake Bay holds a special place in the hearts of many. Find your connection to the bayscapes, breathe in their slightly salty air, taste the flavors of seafood freshly prepared, and feel the freedom of being on the water. The bay has sustained generations through its bounty and its spiritual rejuvenation, and you too can immerse yourself in its treasures.

Select one or more quintessential Chesapeake Bay cities and towns as the starting point for your adventure. Each town has its own personality and displays a distinct mood. Some provide a serene retreat, while others beat with the thriving energy of the city.

In bustling Annapolis, America’s sailing capital, for example, watch billowy white sails racing against a cerulean sky. In Rock Hall, listen to the steady rhythms of a working fishing village. There are plenty of opportunities to explore your Chesapeake in ways that synchronize with your own pace.

Along the way, you’ll find places to access the waterfront and sail on a historic oystering vessel or charter boat. Lighthouses complete the scene, some of which can be toured. Charming main streets with locally-inspired architecture lure you to peruse unique shops and galleries with friendly staff. Seafood restaurants entice with the aroma and flavors of today’s catch.  And there’s places to feed the mind and curiosity too at numerous maritime and decoy museums.

Thread together several towns or points of interest by traveling on a themed scenic byway, such as the Chesapeake Country National Scenic Byway. Come back and explore a new area until you’ve visited them all.

How to Travel around the Chesapeake Bay

Quintessential Bay Towns

Chesapeake Experiences

Where to Stay

Trip Suggestions 


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