Oldtown is a unincorporated community in Allegany County, Maryland along the North Branch Potomac River. It was established in 1741 by Thomas Cresap, who built a trading post along an old Native American trail. The settlement was called "Shawanese Old Town" because it was the site of a Shawnee village abandoned about a decade earlier. In later years the explanatory prefix was dropped from the name and the place because known simply as "Oldtown. " Cresap's son Michael Cresap was born at Oldtown. A post office was established there on May 26, 1870. Oldtown is connected by a one-lane low water toll bridge to Green Spring in Hampshire County, West Virginia. The "Chesapeake & Ohio Canal" reached Cumberland, MD from Georgetown (Washington, DC) in 1850 by way of Oldtown at Milepost 166.5. The "Baltimore & Ohio Railroad", located just across the Potomac from Oldtown had reached Cumberland eight years earlier. The canal finally closed operations as a carrier in 1924 due to flood damage. The B&O Railroad, now CSX, continues to be a major carrier; and it is used daily by Amtrak's "Capitol Limited" between Washington, DC and Chicago. The "Western Maryland Railway" expanded west, from Big Pool, MD to Cumberland, MD as a Class-I Railroad in 1906 with the mainline being constructed through Oldtown complete with a train station located at the lower end of town. Passenger service ended on the Western Maryland Railway between Cumberland and Hagerstown, MD on May 30,1953. Afterwards it was not uncommon for B&O Passenger trains to be rerouted over the WM through Oldtown. The last scheduled mainline trains through Oldtown occurred on May 12,1975 for freight, and May 21,1975 for a Chessie System Passenger Special. The line was officially abandoned as part of the "Chessie System" consolidation and all WM trains began running on the nearby B&O. A Chessie System work train pulled up the rails through Oldtown in June 1976.

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