Christopher Smith established Smithsburg in 1814. It grew with traditional rural character—a commercial core anchoring a compact residential community with churches. By the middle of the century, Smithsburg was thriving with taverns, blacksmiths, tailors, wagon shops, and dozens of houses.

By 1873, the Western Maryland Railroad connected Baltimore, Hagerstown, and the C&P Canal at Williamsport. It also connected to Smithsburg, contributing to rapid changes in the character of the town. Later, when the Cumberland Valley Line connected to the Norfolk and Western in nearby Hagerstown, vast additional markets were opened from New England to the Gulf Coast.

But the railroad also created similar opportunities for the developing areas to the west. Cheap midwestern grain flooded into the eastern markets, spelling potential trouble for towns like Smithsburg. Disaster was averted, however, when peaches were found to grow well on the South Mountain slopes—and by then refrigerated train cars were available to distribute the fruit nationwide.

The economic boom that started with the arrival of the railroad continued, and in the 1930s Smithsburg became the banking and trade center for the fruit growers of the region. For years, the town experienced modest growth, but its physical character changed little within and around the limits of the old town.

After World War II, business in the town center declined as the population found a new mobility and competition from Hagerstown-based commercial centers increased. Businesses moved to the regional shopping centers, leaving downtown buildings vacant or under-utilized.

At the end of the 20th century, improved roadway access across South Mountain to the employment centers in the Washington-Baltimore metropolitan area fueled interest in the development of residential properties in Smithsburg. Annexation of “new town” areas significantly increased the town’s size and potential population. But the “old town” retained much of its original architectural quality and still remains relatively untouched by negative aspects of post-WWII development.