Sharpsburg is best known as the site of the bloodiest battle of the Civil War (in terms of the most casualties in a single day) and the first major engagement on Union soil, fought in 1862. However, Sharpsburg was founded nearly a century prior, in 1763, and by the time of the war it was a thriving commercial center, supporting the local agricultural community and with trade and transportation via the nearby Chesapeake and Ohio Canal. The gridded town plan developed by founder Joseph Chapline called for setbacks to form a town square at its crossroads, now occupied by the Masonic Hall and former Kretzer’s Market (1887; 100 E. Main Street) and by the Sharpsburg Library and Town Hall (1911; 106 E. Main) built by the International Order of Red Men (IORM).
Most of the early buildings were constructed of logs (hidden under siding), including at least thirty-five extant houses along Main Street. Sharpsburg’s architectural highlights include a number of early cut-stone Georgian houses, such as the story-and-a-half William Good House (c. 1780; 107 E. Main), Piper House (1792–1804; 200 E. Main); Kretzer Homestead (c. 1790; 128 E. Main); and the William Chapline House (1789; 109 W. Main). Brick Federal houses followed, represented by the Grove-Delauney House (c. 1820; 100 W. Main). A number of houses are combined with a commercial function, such as that of physician Joseph C. Hays (c. 1823), set back along the town square at 105 W. Main. The wing included his medical office, later a dry goods store and, in 1920, was remodeled as Sharpsburg Bank. Also noteworthy is the Jacob Highbarger House (c. 1832; 201 W. Main), a Greek Revival-influenced limestone house and attached shop built by house carpenter Jacob Highbarger. His shop is a rare example of exposed hewn log construction with corner posts and diagonal bracing.
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