Founded in 1767, Middletown is located in the fertile valley between Frederick and Boonsboro, and like many towns in western Maryland, it owes its genesis to an advantageous position along trade routes. However, it was the opening of the interurban electric railway from Frederick that shaped Middletown’s growth starting in 1896. Large houses designed in a variety of popular late-nineteenth-century architectural modes, many used as boardinghouses for travelers, were built on newly subdivided lots in a former orchard along E. Main Street, particularly in the 300 and 400 block. The wide setback here is a remnant of the interurban right of way. Bypassed by the new U.S. 40 between Frederick and Hagerstown in 1936 and further placed off the beaten track by construction of I-70 in the 1960s, Middletown is now a bedroom community that retains much of its historic commercial and housing stock.
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