Henry Smeltzer Farmstead

The Stonebraker and Harbaugh–Shafer Building in Middletown, Maryland was built circa 1830 with a residential section to the east and a commercial section to the west. The Federal style building incorporates Greek Revival detailing in the interior.The Stonebraker and Harbaugh–Shafer Building was listed on the National Register of Historic Places in 2002. It is included in the Middletown Historic District.

Middletown is a town in Frederick County, Maryland, United States. The population was 4,136 as of the 2010 census. Located in the Middletown Valley that stretches between the Catoctin Mountains on the east and South Mountain on the west, the town reportedly gained its name from its location midway between those ranges.

The Middletown Historic District comprises the historic center of Middletown, Maryland. Middletown became the chief community in the Middletown Valley in the late 18th century, retaining its importance until the 1930s, when the expanding influence of Frederick, Maryland, the construction of a bypass on US 40 and the abandonment of the Hagerstown and Frederick Railway produced a gradual decline. The historic district preserves many mid-19th-century buildings in the central downtown area. To the east, the district includes early 20th-century houses built along the trolley right-of-way, forming a streetcar suburb. The Airview Historic District includes a related area of early 20th century development to the east of town along the National Pike, separated from the main district by a section of newer development.

Spoolsville is an unincorporated community in Frederick County, Maryland, United States. Bowlus Mill House was listed on the National Register of Historic Places in 1996.

The Bowlus Mill House is a historic home and farm complex, located at Spoolsville, Frederick County, Maryland, United States. It consists of the house built of narrow courses of flat cut stones, a frame bank barn on a stone foundation, and a small frame shed. The 2+1⁄2-story house with an exposed basement was built about 1800, and reflects the Germanic influence typical of the region in the period.The Bowlus Mill House was listed on the National Register of Historic Places in 1996.

Middletown High School is a high school located in Middletown, Maryland, United States. First established in 1888, the school opened in its current building in April 1974.

The Airview Historic District is a district of 12 houses built between 1896 and 1930 on each side of East Main Street in Middletown, Maryland. The district was developed to take advantage of the Hagerstown and Frederick Railway, which paralleled what was then known as the National Pike, and is an example of a small-scale streetcar suburb. The subdivision was subdivided from the Kefauver farm and included a trolley stop in front of developer Lewis Kefauver's house. The trolley right-of-way is still visible in the deep setback between the street and the sidewalk in the front yards of houses on the north side of the street. The subdivision's location in a then-rural setting view with its expansive views made the suburb attractive for retiring farmers.The Airview Historic District is now part of Middletown, but is separated from the Middletown Historic District by a section of newer development.

Middletown Valley, also historically known as Catoctin Valley, is a valley in western Frederick County in the state of Maryland.

Shafer's Mill is a house near Middletown, Maryland, built in the early 19th century. The Federal style house was built for John Shafer, Jr., and was occupied after his death by his son, Peter. The Shafers operated four mills in the Middletown area. The house, however, was never operated as a mill.

Bennies Hill Road Bridge is an iron bowstring arch bridge over Catoctin Creek near Middletown, Maryland, United States. It is one of two remaining bridges of its type in Maryland that remain in their original locations. The bridge was restored in 2009.

The Henry Shoemaker Farmhouse is a circa 1810 Federal style farmhouse which was involved in the Battle of South Mountain in 1862. Located near the eastern end of Turner's Gap, the house was the center of a Union encampment and served as a field hospital.The Henry Shoemaker Farmhouse was listed on the National Register of Historic Places in 1989.

The Daniel Sheffer Farm is a historic home and farm complex located at Middletown, Frederick County, Maryland, United States. It is dominated by the two story brick main house, which was constructed between 1840 and 1850. Outbuildings include a stone spring house, a large wood-frame barn, constructed about 1900, and several wood-frame outbuildings including a corncrib, a wagon shed, three frame wood sheds, two tractor sheds, and a chicken house. A concrete block milk house and terra cotta silo were added to the complex in the 1930s. In September 1862, the property served as a temporary hospital for wounded soldiers during the Battle of South Mountain in the American Civil War.The Daniel Sheffer Farm was listed on the National Register of Historic Places in 2001.