In 1712, Philemon Lloyd of a prominent family of the Maryland Eastern Shore, had a lot surveyed for him which was to be used by the drummer of the town. The drummer, an alternative to the town crier, was unique in Maryland. His duties were to convey public information through a variety of complex drumbeats. One of his duties was to call Maryland's General Assembly to session. If a member of the assembly failed to appear by the third drum roll, he was fined 100 pounds of tobacco. The drummer was also charged with keeping the town gate. The gate was to keep cattle out of town and was located one block from Church Circle on what is now West Street.
William Butterfield was a drummer in the 1700's. He was paid five pounds per year for beating the drum and keeping the gate and he could earn fees for beating the drum on special occasions. In all, his earnings must have been adequate, for a court order established fines for beathing the drum at unseemly hours of the night. The order indicates that drummers sometimes indulge in enough rum and madeira at one of the taverns in Annapolis as to encourage jubilant and rowdy behavior.
Drummer's Lot, lot 49, has a title chain that includes some of the most important names in Maryland's history: Chew, Dulaney, Dorsey, Pica, Bordley, and others.
In 1772, Thomas Hyde, a respected merchant and civic leader, acquired a long-term lease on the lot from Nathan Walters who was the mentor of portrait painter Charles Wilson Peale. Hyde had the front part of what is now the Maryland Inn constructed on the lot. In 1782, Hyde advertised for sale. It was described as "an elegant brick house adjoining Church Circle in a dry and healthy part of the city, this house is 100 feet front, 3 story high, has 20 fire places and is one of the first house in the state for a house of entertainment".
The Inn remained a popular place for lodging throughout the 19th century. It was acquired by the Maryland Hotel Company in 1868 and remained the most prominent Annapolis hotel and favorite rendezvous for important national, state and military visitors. in 1898, Spanish Admirals as prisoners of war were quartered there. By World War I, the Inn's facilities were outmoded and many of its rooms were converted into offices and apartments. There were several owners in the next several decades and in 1953 owners who became aware of the Inn's importance in Maryland's history acquired it. They began restoration designed to return its colonial appearance and to adapt ts historic accommodations to modern requirements. Since 1970, the Inn's present owners have completed its restoration. Colors used are those of the Inn's Victorian period, when it significantly expanded and many antique furnishings were added to guest rooms and public spaces.