Chesapeake Bay Bridge.
Travel Around the Great Chesapeake Bay Loop
Chesapeake Bay Bridge.
The Great Chesapeake Bay Loop depicts the region surrounding the Chesapeake Bay on both the eastern and western shores. The loop includes the waterside communities on Maryland’s Eastern Shore, the Upper Chesapeake, the metropolitan centers in Central Maryland, and the peninsulas in Southern Maryland created by the wide Patuxent and Potomac rivers.
Across the middle of the Bay, the Chesapeake Bay Bridge connects the Eastern Shore of Maryland with the Annapolis area on the Western Shore. Crossing the Chesapeake Bay Bridge is an experience to remember. Its elegant, dual spans provide height for views up and down the Bay for passengers riding along.
At the mouth of the Bay, the 17-mile Chesapeake Bay Bridge Tunnel is an engineering marvel connecting the Chesapeake’s eastern and western shores in Virginia. These connections allow you to circumnavigate the Bay or take a shortcut and plan your own adventure.
Take a Maryland Scenic Byway to explore America’s largest estuary through several shorter road trips. Maryland Scenic Byways weave together quintessential waterfront Chesapeake Bay towns, attractions, natural and historic sites, and scenic views. They’re a great choice for weekend getaways, midweek escapes or week-long vacations. Pick one listed below and start making your Chesapeake memories.
To jumpstart your vacation planning, check out some ready-made trip ideas.
The colonial port of Chestertown graces the banks of the Chester River, offering restaurants, shops and inns.
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.
Tubman Statue at Dorchester County Courthouse, Cambridge, Maryland.
Explore the secret network of trails, waterways and safe houses used by enslaved people fleeing north from Maryland’s Eastern Shore into Delaware and beyond. The incomparable beauty of the landscape, which provided both challenges and opportunities for freedom seekers, will leave you breathless.
Dr. Mudd House Museum
Follow the escape route of John Wilkes Booth that led to his apprehension. Booth, one of history’s most notorious assassins, fled from Washington, D.C., and hid for several days in Southern Maryland before being cornered. Along the way, travel through rolling hills dotted with farms, woodland and waterways.
St. Clement’s Island where the first English explorers landed in the colony of Maryland.
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. Taste freedom on the wind. Witness the divine in every ripple of the river. Explore Southern Maryland, cradle of American religious liberty.
Star-Spangled Banner Flag House & Museum
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.”
Annapolis Harbor City Dock.
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.
Canvasback Cove on the Susquehanna River in Havre de Grace.
Discover waterfront towns steeped in maritime history with sweeping views along the Susquehanna River. The Lower Susquehanna Byway serves up extraordinary birding, paddling, hiking and fishing spots as well as plenty of opportunities to shop, dine and explore charming small towns.
