Even before its founding in 1767, Middletown, Maryland has welcomed travelers on the Old National Road. Tradition has it that a young Lt. George Washington, looking from South Mountain across the Middletown Valley, proclaimed it the most beautiful place he had ever seen. That sentiment is as true today as it was in Washington’s time. Stately historic homes, expansive views of the valley, and an enduring spirit of community convert many a traveler into resident.
For a small town, we are packed with hidden treasures — far too many to fit into one standard walking tour. To encourage in-depth exploration, we have adopted six separate tours that focus on history, architecture agriculture, business, and people who have contributed to Middletown’s rich and diverse heritage. The word heritage is defined as ‘the traditions, achievements, and beliefs that are part of the history of a group of people.’ These six Heritage Tours are more than a list of buildings and sites. They form a road map to our collective history. They reveal the countless ways in which Middletown’s story is America’s story.
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 Tour focuses on the places 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 Street Victorian and Airview Historic Districts. 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.
Plan your tours one at a time or group them together. Set out by car, bicycle, or on foot. If you’re pressed for time, a driving tour gives you an excellent overview. Walking or bicycling allows you to fully experience Middletown’s sense of place. Enhance your visit by dining at one of our restaurants, browsing our shops, or joining in on one of our special events. We invite you to discover the many reasons why Middletown is known as Maryland’s Timeless Treasure.