Heritage Walking Tours

Come Experience For Yourself

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.

Canaan Tour

Local histories report that the western end of Middletown was settled first and one of our oldest surviving houses, the Smithfield House, is located in the western section of Middletown at 16 Walnut Street. Settlement starting at the west end of town makes sense because of the proximity to the source of water, Catoctin Creek, and the naturally occurring flatter lands.

In addition to the Smithfield House this area is home to early and important industries that supported the many farmers of the Middletown Valley, including a tannery and creamery (both no longer extant).

The tannery processed animal skins into workable leather. At this complex, the skins were cleaned and soaked in water containing tannin to preserve them and give them a rich brown color. This process required large numbers of trees to supply tannin, as well as a reliable source of fresh water. Tanner’s Branch still runs from a underground spring near Main’s Alley, behind the buildings on the south side of Main Street, and down to Catoctin Creek.

The Creamery stood in what is now the Creamery Row neighborhood. Before the late 1800s, farmers generally produced enough milk, butter and cheese to sustain their families. At the turn of the century, with the migration from farms into the cities, milk production grew to a large-scale industry. Diary farmers brought milk to the Middletown Creamery, where it was processed for sale.

Middletown Creamery

Many structures in this area are built close together, nestled into the hills on the north side of the road. Look for the vernacular Germanic building traditions of the mid 1800s — front facades with a window-window-door arrangement, and ground-floor entries to the basement instead of the main living quarters.


Catoctin Creek Bridge (ca. 1850, 1920) During the Civil War, just before the 1862 Battle of South Mountain, Confederate soldiers destroyed the original bridge. It was rebuilt on stone abutments. In the 1920s, as part of the federally funded Good Roads Program, the covered bridge was replaced with a concrete arch bridge.

Catoctin Creek Bridge (ca. 1850, 1920)

Middletown Covered Bridge (ca. 1809, 1868) According to an article in the Baltimore Sunpapers in October 17, 1937: “There is only one covered bridge that can be definitely dated; it stands near Middletown, Frederick County, and was put up in 1809.” This bridge is considered by some historians to be the first covered bridge constructed in Maryland and was located approximately 0.6 miles southwest of the National Road, on Bidle Road. Unfortunately, the bridge is no longer standing.

Middletown Covered Bridge (ca. 1809, 1868)

504 West Main Street (ca. 1850)

Known as the Jacob Rudy House, this was where the future president Lt. Col. Rutherford B. Hayes received care after he was wounded at the Battle of South Mountain. Lucy Hayes soon arrived to care for her husband; and she later volunteered as a nurse.


10 Walnut Street (1929)

The original Schlosser Tannery stood on this site until 1915, when Calvin and Lola Gladhill relocated their furniture business from Myersville to Middletown. Gladhill’s sold a variety of goods: furniture, wagons, buggies, carriages, as well as funeral related services and caskets. The original structure was razed in 1929, replaced by the present structure housing their furniture showrooms and workshops. One of the town’s oldest continuously operating business, Gladhill Furniture celebrated their 100th anniversary in 2015.


14 Walnut Street

The Gladhills lived in the house directly west of the store on Walnut Street. This two-story, three-bay house with a central, cross-axis gable features sidelights and transoms surrounding the front door — all typical of houses built in town in the mid-19th century. Note the early-20th century cast concrete porch columns designed and modified Corinthian style. They are mounted on rusticated cast-concrete block plinths, first used in Middletown at Gray Haven, 709 East Main Street.


16 Walnut Street (ca. 1840)

The town’s oldest known dwelling is the original log section of the Smithfield House. The log structure was built around 1730 by gunsmith Frederick Lauber. Nearby stood the tannery complex that played a role in the Civil War. According to a report dated March 1, 1863, by Dr. Jonathan Letterman, “At Middletown, ten buildings were occupied for hospital purposes, from the day of the battle of South Mountain.”


210 West Main Street (ca. 1860)

This two-story, four-bay house once belonged to tanner John Appleman. It was probably constructed of logs, though today it is sheathed in vinyl siding and sits on a raised stone foundation with a front porch supported by Doric columns. After the Battle of South Mountain, a wounded soldier made his way to Middletown, where his wife had family members. He stopped at this house by chance and learned that the Applemans were related to his company lieutenant.


308 West Main Street (ca. 1850)

This large house was associated with the Schlosser Tannery. The tannery was a large complex with numerous brick buildings. In addition to its historic association with the tannery, the entrance with sidelights and transom is one of the best examples of the Greek Revival style in Middletown.