The engineering marvels of the Chesapeake Bay Bridge (across the middle of the Bay) and the Chesapeake Bay Bridge Tunnel (across the mouth of the Bay) enables road travel around the Chesapeake Bay in one big loop; or an upper Bay Loop and a Lower Bay loop; or a figure-8 path.
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.
1 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.
2 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.
3 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.
4 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.”
5 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.