Port Tobacco is the smallest incorporated town in Maryland; only 15 people lived there in 2010. The town was established in 1727 and in the following years became the second largest city in Maryland and also the county seat of Charles County. Port Tobacco began to decline for a variety of reasons: the railroad industry, La Plata becoming the county seat in 1895, and tidal forces cutting off access to the Chesapeake bay.

Port Tobacco is a small town, but it is full of history. The first President under the Articles of Confederation was from Port Tobacco. There have been many other important political figures from the town (including the co-conspirator to John Wilkes Booth). Port Tobacco is also important due to numerous archaeological sites which give information about the Native Americans and colonists who used to live here.