Bennies Hill Road Bridge

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.

The Poffenberger Road Bridge, near Jefferson, Maryland, is a wrought iron bridge by the Wrought Iron Bridge Company of Canton, Ohio. The bridge is similar to the Fourpoints Bridge elsewhere in Frederick County. The bridge is a single-span double-intersection Pratt truss. It was built circa 1878 and remains in daily use.It was listed on the National Register of Historic Places in 1978.

The Henry Smeltzer Farmstead is a historic home and farm complex located near Middletown, Frederick County, Maryland, United States. It includes a two-story six-bay brick farmhouse dating to about 1832, a frame bank barn ruin, and several rusticated concrete block silos. A concrete block slaughter house, weighing house well house and holding pens complete the complex, which was associated in the early and mid-twentieth century with Main's Meats in Middletown. The house is built into the hillside as a "bank house", with its cellar above grade on the south side. The front and rear elevations feature porches across their widths.The Henry Smeltzer Farmstead was listed on the National Register of Historic Places in 2010.

Broad Run is an unincorporated community in Frederick County, Maryland, United States. Broad Run is located on Maryland Route 383, 4.5 miles (7.2 km) southeast of Middletown.

Lewis Mill Complex is a historic grist mill complex located at Jefferson, Frederick County, Maryland. The complex consists of seven standing structures, a house foundation, and the remains of an earlier millrace. It centers on an early 19th-century three-story brick mill structure with a gabled roof. The mill complex served German immigrant farmers in Middletown Valley between 1810 and the 1920s. It was rehabilitated in 1979-1980 for use as a pottery shop. Also in the complex are a stuccoed log house and log springhouse built about; a frame wagon shed and corn crib structure and frame barn dating from the late 19th century; and early 20th century cattle shelter and a frame garage.It was listed on the National Register of Historic Places in 1982.A trombe wall was installed on the south wall of the mill in 1980 to heat the business and living quarters. Solar panels were installed on outbuildings in 2011.

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 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.

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 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.

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

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.

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.