Although the first land purchases were transacted in 1681, shortly after William Penn received the charter from King Charles II, the first buildings did not appear in the forested valley until 1700, now known as the Downingtown Log House. Thomas Moore erected "a water corn mill" in 1716 and Roger Hunt established a grist mill in 1739. During the 18th century the hamlet aquired the colloquial name of Milltown or sometimes Downings' Town.
Travel betwen Philadelphia and Lancaster was a two journey via stagecoach. Since Milltown was the halfway point, several inns were established: The Ship Inn, circia 1730; the King-in-Armes, later known as the Washington Inn, in 1761; The Half-Way House in 1790; and The Swan Hotel in 1800.
The village changed when the railroads were constructed through the town in the 19th century. The new mode of transportation caused the demise of the stagecoach line and the shops near the Washington Inn became homes. The Railroad House or Pennsylvania House was built to accommodate the travelers.
Chester County Court approved petitions for the village to be incorporated as the Borough of Downingtown on May 12, 1859. Within a few years almost one hundred men showed their loyalty by serving in the Civil War.
The English Quakers were joined by the Irish and free blacks, with the Italians and Germans arriving at the turn of the century. They worked in the town's mills and on the railroads, soon building boomed.
New services were required to fulfill the expanding needs of the town. The Citizens Holding Company was formed to build the municipal building in 1926.
Today, the citizens want to maintain their man-made environment and prevent deterioration of their small town. The East Lancaster Avenue Historic District was the first designated historic district in Downingtown and was placed on the National Register in 1979.
