Charlestown: A historical gem at the top of the Chesapeake Bay

Charlestown Town Commissioner Karl H. Fockler re-enacts Lt. Col. Nathaniel Ramsey.

A settlement well before Maryland became a state, the sleepy hamlet of Charlestown, located on the northeastern-most shore of the Chesapeake Bay, and less than a 30-minute drive from Aberdeen, has several historical connections.

Charlestown was formed in 1742, by an act of the Maryland Assembly which stated, “the encouragement of Trade and Navigation is the surest means of promoting the happiness and increasing the riches of every country . . . [and] . . . there being as yet no [town] settled at or near the head of the Chesapeake Bay…” The colonial village became the first incorporated town in Cecil County, and briefly served as the County Seat.

The town, serving as a connection between Baltimore and Philadelphia, was meticulously planned, said local historian Audrey Edwards. Seven streets were planned from north to south, and seven were planned from east to west, each named after prominent and wealthy Baltimoreans. Curvy roads were designed to accommodate horses and wagons, as the animals wouldn’t be able to maneuver hills, she said.

A view of Charlestown, Maryland, including the local fire house.

Several historical figures made their way to Charlestown over the years, including Benjamin Franklin, George Washington and American artist Charles Willson Peale.

The Wellwood, a historic restaurant in Charlestown, dates back to the late 1800s. Orignally a private hunting and fishing club, it evolved into a country and yacht club that attracted the likes of Theodore Roosevelt, Calvin Coolidge and Joseph Cannon, the powerful Speaker of the House under Roosevelt and William Howard Taft. The Wellwood is best known for the 1918 barbecue during which 28 senators, 16 governors and several colonels gathered there and listened to a pitch from restaurant founder Louis H. Eisenlohr and Riley Wilson encouraging America to make Alaska a state.

The duo had spent time there and were fascinated with the area, said Larry Metz, the current owner of the Wellwood.

“He was 40 years above his time,” he said.

The town was also home to Lt. Col. Nathaniel Ramsay, a lawyer who served under Gen. George Washington in 1778, when he was wounded at Monmouth, New Jersey, and taken prisoner by the British. He was later a U.S. Congressman.

The town’s treasurer, Karl H. Fockler, is a Ramsey reenactor. With local landmarks throughout the town, including four historical markers, he said the area is popular with people who appreciate history.

A view of Holloway Beach in Charlestown, Maryland. On a clear day, a view of as many as 30 miles can be seen.

“It was integral in part of the defense of the upper part of the Chesapeake Bay,” he said.

Today, Charlestown is home to two restaurants, a school, a church, a firehouse, a post office and a marina with several docked boats. In recent years, the town population increased from 1,019 in 2000 to 1,183 in 2010, according to U.S. Census data.

At Holloway Beach, which was a popular tourist destination prior to the the prominence of the car and the construction of the Chesapeake Bay Bridge, which gave access to Ocean City, guests can see up to 30 miles away on a clear day.

Andy Thompson, Town Council president, said the population has gotten younger in recent years; he credits the popular Charlestown restaurants as a factor attracting people to the area.

“I think the town is doing well today,” he said.

For more information about local activities, events and attractions in Charlestown, visit