CHARLESTOWN — Now one of Cecil County’s smaller towns, when Charlestown was erected in 1742 it was a land of great promise and commerce.

The town was such a significant port of entry that its founders drew chances to see which lots they could possess. One of the most prized lots to be had was Lot No. 82, which went to Zebulon Hollingsworth. Sitting on Market Street, the main thoroughfare next to the crucial Market Square, Hollingsworth was listed as an “Innholder” on his deed and noted that he served as a town commissioner from the time of the town’s creation.

A widower with seven children under the age of 13 years old, he married Mary Jacobs in 1741 and fathered seven more children in quick order. Having 14 children and a wife crowded into his home in Charlestown, Hollingsworth eventually moved his family to a farm known as Friendship near the mills on the Elk River.

The valuable Lot No. 82 therefore, with a handsome dwelling, would eventually fall to Capt. Jonas Owens in 1804, before passing to the Black family. By 1858, Simon Martenet’s map of Cecil County shows that the three old structures on Lot No. 82 were still in existence and the three structures, now connected, were “a store, dwelling and hotel.”

It is interesting how the property, known as the Red Lion Tavern, came to be moved from Owens to the Black family. Owens kept a store with a partner, John Hasson, and apparently after Owens died in 1829, Hasson continued the operations. In 1802, he wed Nancy Meeks, of Port Deposit. They had two sons, John and James Hasson, before John Hasson died, leaving his widow to continue operating the store and hotel business. In 1809, she remarried to Capt. John Nelson Black, who served in the 30th Regiment of the Cecil County Militia.

Black followed Hasson as Nancy’s husband, but as storekeeper and on May 14, 1809, as a Charlestown commissioner when the board elected him to replace Hasson. By 1823, he would serve as the town’s elected registrar.

The couple had four children — William Washington Black, Martha Jane, John Nelson, Jr., and Rebecca. As the family grew, Black made improvements to the Red Lion Tavern, including water pumps, a carriage house, cart house, hay house, two barracks and a poultry house. He fenced in the property and built a coffee house in the garden. When the East Market Street house burned down, he moved the family into his wife’s other property, the Indian Queen alongside. Eventually, the Red Lion would merge into the Indian Queen Hotel.

Obviously, the historic structure has a relatively complex development over time. The core of the building is essentially one log room that was added onto over time. Serving as a hotel for years, the Indian Queen portion lost ground to the elegant Cecil House on Bladen Street. Black, however, adapted the Indian Queen to serve as a boarding house.

Both the store and the hotel made boarding house could not weather the nationwide economic depression of 1894 though, which proved disastrous for Charlestown as a whole. A Black descendant, Isabell Black Barnes, took over and moved the store counters to the loft to rent the store to tenants and began selling off lots. She could not afford to maintain the stables.

The home would fall to Mrs. Edna Black Caulk in 1964, who held the last life interest in the Black family legacy of the home. The ancient structure was brought to the attention of the Maryland Historic Trust by a young architect, James T. Wollon, Jr., and the property was listed on the state’s register as well as the National Register of Historic Places (1975). Other owners restored the property to its singular beauty of today.

The home at 322 Market St. is now fully restored to showcase old world charm and modern convenience with four bedrooms and two bathrooms in the 2,172-square-foot space that boast seven fireplaces and exposed beam ceilings. It was sold in June of 2017, and remains a bastion of interest as part of the storied history of one of Charlestown’s most intriguing colonial properties.

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