Middletown’s roots lie in the west end of town in the area once known as Canaan, settled around 1750. As the town quickly grew into the commercial and social hub of the agrarian valley, homes and businesses spread eastward along what is now the Main Street Historic District and south along Jefferson Street. Our Religious Heritage focuses on the place of worship that have always been central to the community.
After the Civil War, Middletown continued to expand east along the Old National Road (U.S. 40 Alt.). In the late 1800s came the town’s first ‘suburbs’ on Old East Main Street, large houses financed by fortunes from local agriculture and industry. The Hagerstown and Frederick Electric Railway sparked the early 20th century’s final major expansion in the East Main Victorian Historic District & East Main Airview Historic District.
As modern highways replaced the old roads and railroad, Middletown’s prominence as the valley’s commercial hub diminished. Its spirit lives on, as reverence for the past helps shape a prosperous future.
Printed brochures are available at Town Hall, the Main Street office, or at the Frederick County Tourism Center. Download individual tour brochures by visiting the individual tour page.
The Smithfield House, 16 Walnut Street
Canaan
19 W. Main Street (c. 1870)
Main Street Historic District
Jefferson Street
Jefferson Street
36 East Main Street
Old East Main Street
401 E. Main Street
East Main Victorian Historic District
Trolley
East Main Airview Historic District
107 W. Main Street