Exploring Stories of the Chesapeake

During these days of social distancing, the Stories of the Chesapeake Heritage Area has several options available to the public that are perfect for a family to learn and explore this summer. For example, take a ride through, or explore from home, the Stories of the Chesapeake. Two nationally recognized scenic byways and a variety of driving tours introduce drivers to one of the last truly special landscapes in the Mid-Atlantic region and gain an appreciation of the working life of Eastern Shore farmers, merchants, and watermen while following in the footsteps of great American heroes. Here is a sampling of the driving tours:

Frederick Douglas Driving Tour

Born a slave in Talbot County, Frederick Augustus Washington Bailey escaped to freedom in 1838 and went on to become Frederick Douglass, the great 19th century abolitionist and civil rights reformer. Much of the landscape of Douglass’s youth in Talbot County, which he so vividly describes in his writing, remains intact today. Visit https://frederickdouglassbirthplace.org/driving-tour.

Underground Railroad All-American Road

Take a powerful and inspiring road trip to the places on Maryland’s Eastern Shore and through Delaware where Harriet Tubman lived, worked, worshiped, and led others out of slavery. Visit https://harriettubmanbyway.org.

Chesapeake Country National Scenic Byway

Come celebrate life on Maryland’s Eastern Shore. Experience the Chesapeake Bay and observe watermen bringing their bounty to shore. Visit historic towns and learn about the area’s rich history and culture. Travel through scenic stretches of productive farmland and see farmers work their fields. Visit http://chesapeakebyway.org.

Historic Towns

In addition, the Stories of the Chesapeake invites everyone to explore area heritage sites from either the comforts of home or on-site. All these historic towns are on the Chesapeake Country Scenic Byway. Travel through scenic farmland punctuated with breathtaking views of the Chesapeake Bay and local rivers. Let the Chesapeake Country Scenic Byway introduce you to one of the truly special landscapes of the Mid-Atlantic Region and gain an appreciation for the working life of our farmers, watermen, and merchants. Here, we focus on important historic towns on the Mid Shore:


The oldest continuously operating courthouse in the United States sits in the heart of historic Centreville along with the only known sculpture of Queen Anne outside of England. Historic houses, including Tucker House and Wright’s Chance, give a glimpse of life in early America – both are featured prominently on the Centreville Heritage Walking Tour. Nearby activities include the Corsica Water Trails and Conquest Preserve.



Located on the scenic Chester River, Chestertown is one of the few National Register of Historic Preservation Landmark Districts. The county seat of Kent, the Eastern Shore of Maryland’s oldest county, Chestertown was founded in 1706 and served as a major port of entry during colonial times. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander, browse and admire. A visit to Chestertown’s Historic District is especially worthwhile, and includes a number of fine colonial residences, as well as some superb examples of later and more elaborate architectural styles. Second largest district of restored 18th-Century homes in Maryland, Chestertown is also home to Washington College, the nation’s tenth oldest liberal arts college, founded in 1782.



The Town began as a tiny settlement on the Choptank River about 1781. It quickly became a trade center for a fairly wide agricultural area. In the days when commerce between the Eastern Shore and Baltimore was chiefly by water, Denton Wharf on the Choptank River was a busy loading point.




Voted one of the best small towns and one of the top 100 small arts communities, Easton is as sophisticated as it is lively. Featuring a world-class theater, renowned art galleries and impeccably curated museums, it’s the heart of the Shore’s arts and culture scene. This mini metropolis draws international artists, musicians and cultural connoisseurs to a series of acclaimed festivals each year. And it’s a foodie town to boot, chock-full of hidden culinary gems. Easton also has “The Hill,” one of the oldest free African American communities in the country.


No Comments Yet

Leave a Reply

Your email address will not be published.

Get in Touch

Allison Rogers



Attraction Magazine

PO Box 360
Easton, MD 21601

The Good News Magazine
Serving the Eastern Shore for more than 40 Years!