7 Old-World Towns to Visit in Chesapeake Bay

The Chesapeake Bay has served a critical role in the development of the original 13 colonies and American history at large. Stretching across Virginia and Maryland, it was first discovered by Europeans in the 1500s and would see permanent settlements under the English in Roanoke Island and Jamestown. During the American Revolution, the Chesapeake played a crucial role in the climatic Battle of York in 1781.

Today, the bay is filled with historic towns that you can visit. You’ll discover historical cruises, beautiful lighthouses, the place where the Treaty of Paris was signed ending the American Revolution and much more. Here are seven old world towns in the Chesapeake Bay area to add to your travel plans.

St. Michaels, Maryland

The area around St. Michaels was a major center for tobacco farming in the mid-1600s. It would earn its name in 1672 when the Christ Episocapal Church of St. Michael Archangel parish was set up in town. St. Michaels was known for ship building until after the War of 1812. It keeps this history alive at the Chesapeake Bay Maritime Museum, which features an 18-acre waterfront campus, exhibits, artifacts and the 1879 Hooper Strait Lighthouse. Just by the museum, you can take the Patriot Narrated Historical Cruise which will guide you by the Miles River and give you the chance to see historic homes and other sites. You can also take a historical walking tour to see some of these houses up close such as Victorian era homes, the Snuggery or the Dr. Dodson House built in 1799 or 1800.

Havre de Grace, Maryland

Home to just under 15,000 people Havre de Grace was first discovered by John Smith in 1608 during one of his expeditions. By the late 1600s, the town site was used a center for a ferry up the Susquehanna River. The town itself gets its name from General Marquis De Lafeyette who said the area reminded him of the French city of Le Havre. The town was officially founded in 1782, and has a great deal of history you can discover at its local museums. These include the Havre de Grace Maritime Museum, and the Keeper’s House Museum at Concord Point Lighthouse, a 44-foot structure built in 1827. You can see one of the original settlers home from the 1790s at the Steppingstone Farm Museum or see one of the first schools for African Americans at the 1807 Colored School Museum & Cultural Center.

Annapolis, Maryland

Despite being the capital of Maryland, it maintains a small town vibe as just over 40,600 people call Annapolis home. The area was first settled in 1649 by Puritans who were exiled from Virginia. In time, the town would grow into a major entry point for both settlers and slaves. In the crucial early years of the United States from 1783 to 1784 it served as the capitol of the country itself. In the town, you can see this history in person at the Maryland State House built in the late 1700s, where the Treaty of Paris was signed ending the American Revolution. Other spots of interest include the Historic London Town and Gardens, the 1845 Naval Academy and the William Paca House, the home of one of the signers of the Declaration of Independence.

Chestertown, Maryland

First settled in 1706 on the Chester River, Chestertown would become an early center for exported goods, especially tobacco. In 1774, patriots would participate in the Chestertown Tea Party where they threw British tea into the harbor, similar to the more famous Boston Tea Party. There’s many historic spots in Chestertown such as Washington College, first founded in 1782 by George Washington himself. It’s definitely worth a visit to walk its historic grounds. You’ll see many different architectural styles such as Widehall built in 1770 in the Georgian style, the 1740 Watkins-Bryan House, and the 1770 Frisby House. Beyond these structures, you’ll also want to check out the local Farmers Market and explore the local shops like Bee Crafty Antiques & Collectibles and Bart’s Records.

Onancock, Virginia

Captain John Smith called this area the Gem of the Eastern Shore when he explored Onancock in 1608. It would be officially chartered in 1680 and served as a trade port on the Eastern Shore of the Chesapeake Bay. There are few places better to see classic Georgian and Victorian era style homes than Onancock. One such example is Ker Place, which was built between 1799 and 1803 for John Shepherd Ker. Within Onancock, you can also visit one of the best preserved blacksmith shops in Virginia at the Samuel Outlaw Blacksmith Shop, which was in operation until 1991 but since has been turned into a museum. Other buildings in town include the 1778 Scott Hall, 1830 Alicia Hopkins House and the 1825 Harmon House.

Yorktown, Virginia

Yorktown, Virginia was settled in 1634, making it one of the oldest settlements in the state. It first gained a port in 1691 and became a major shipping center. The town is most famous for its role in the climatic battle of the American Revolution where General George Washington defeated General Lord Cornwallis in 1781. American Revolutionary War history buffs will definitely want to spend a day at the American Revolution Museum at Yorktown where they can see living history reenactments of the battle along with artifacts and exhibits. There are several other historic sites in Yorktown including Cornwallis’s Cave, the Moore House where the British surrendered, and the Nelson House, a restored mansion of Thomas Nelson Jr., a governor of Virginia.

Jamestown, Virginia

No list on Old World towns in the Chesapeake Bay would be complete without mentioning the oldest permanent British settlement in America: Jamestown. This town needs no introduction, as most people are familiar with its story of Captain John Smith setting up shop here in 1607 and meeting with Chief Powhatan’s daughter Pocahontas. However, the story goes much deeper than that, and you can learn all about the history of Jamestown at the Archaearium, which features archeological finds from 1607 to 1624 such as armor, weapons, tools, writing slate, tobacco pipes and much more. You can also see the original settlement site at Historic Jamestowne or experience living history reenactors at the Jamestown Settlement, which includes replicas of the three ships that sailed up the Chesapeake Bay.

The Chesapeake Bay only covers a portion of two states, but it contains a great deal of historic places. Within these towns, you’ll find old settlements at Jamestown, see a battlefield at Yorktown or experience the legacy of George Washington at Washington College. The area is a treasure trove for seeing early American architecture both in the early founding days of the 1700s to the Victorian era and beyond. These historic towns are just the ticket for history lovers and explorers alike.