Oldtown was initially called "Shawanese Old Town". It was the site of a Shawnee Amerindian village which eventually was abandoned. The prefix in the name was later dropped and simply became known as "Oldtown". In 1741, Colonel Thomas Cresap settled Oldtown. He was a pathfinder, patriot and frontiersman of what was then the wilderness. Cresap entertained George Washington when he was in Oldtown as a surveyor apprentice. Washington continued to visit Oldtown and Thomas Cresap throughout his life.

Thomas Cresap was active in fur trading, the French & Indian War, and was famous for his dispute against Pennsylvania over the 40th Parallel which was eventually surveyed by Mason and Dixon. Michael, the youngest son of Thomas, was born in Oldtown and was famous for his longrifle skills, in addition for being the Captain of the first southern militia to answer George Washington's call to arms in Cambridge.

The Chesapeake & Ohio Canal spanned from Cumberland to Washington, D.C., in 1850, passing through Oldtown at milepost 166.5. The canal finally closed operation in 1924, due to flood damage.

The Western Maryland Railway was extended from Big Pool, Maryland, to Cumberland in 1906, with the mainline being constructed through Oldtown complete with a train station located at the lower end of town. The last scheduled Western Maryland Railway train was in May 1975. A Chessie System work train pulled up the rails through Oldtown in June 1976.

A post office was established in 1870.

Source: Wikipedia, https://en.wikipedia.org/wiki/Oldtown,_Maryland
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HISTORY OF OLDTOWN