Middleburg, Carroll County, Maryland

Keymar is an unincorporated community in Carroll County, Maryland, United States. The name of the community is a portmanteau of the family name Key (of which Francis Scott Key was a member) and Mar for Maryland. In 1822, Francis Scott Key sold his father's mansion and estate on Pipe Creek near this community. Keymar was likely the name of that estate.

The Little Pipe Creek bridge and viaduct is a 705-foot (215 m) continuous truss bridge with main span and 19 viaduct sections as well as an active railroad trestle crossing Little Pipe Creek south of Keymar, Maryland. Originally constructed by the Frederick and Pennsylvania Line Railroad Company (F&PL). Construction on the trestle began in late 1871, and continued until April 1872. The Pennsylvania Railroad acquired control of the F&PL in 1896, and rebuilt the bridge that year as an open deck riveted iron plate under girder bridge and then again in 1902-1903 using steel in the bridge and trestle. In 1915, the bridge was surveyed as part of the Interstate Commerce Commission's effort to establish freight rates for the parent railroad. The United States Railroad Administration rebuilt the creek span circa 1917. Additional work rebuilding the bridge and trestle was performed from 1982 to 1989 by the Maryland State Railroad Administration. In 1991, the bridge was surveyed as part of the Maryland Historic Sites Inventory. As of 2021, the bridge is in rail service, operated by the Maryland Midland Railway.

The Winemiller Family Farm is a historic home and farm complex located at Taneytown, Carroll County, Maryland, United States. The complex consists of a large two-story brick house built about 1865, a frame bank barn, and several outbuildings. It is a representative example of a type of family farm complex that characterized rural agricultural Carroll County from about 1850 through the early 20th century.The Winemiller Family Farm was listed on the National Register of Historic Places in 2006.

Mt. Pleasant, also known as the Clemson Family Farm, is a historic home located at Union Bridge, Carroll County, Maryland, United States. It is a five-bay by two-bay, 2+1⁄2-story brick structure with a gable roof and built about 1815. Also on the property is a brick wash house, a hewn mortised-and-tenoned-and-pegged timber-braced frame wagon shed flanked by corn cribs, and various other sheds and outbuildings. It was the home farm of the Farquhar family, prominent Quakers of Scotch-Irish descent who were primarily responsible for the establishment of the Pipe Creek Settlement.Mt. Pleasant was listed on the National Register of Historic Places in 1998.

Union Bridge station is a historic railway station in Union Bridge, Carroll County, Maryland. It was built in 1902 as a stop for the Western Maryland Railway. It is representative of the rural railway stations constructed during the late 19th and early 20th centuries. The station's two buildings are arranged with their south façades lengthwise fronting the railroad tracks.The railroad operated a major railroad car shop adjacent to the station from the late 19th century until the 1950s. The shop buildings were demolished in 1964.The station was listed on the National Register of Historic Places in 1976 as Union Bridge Station.

Union Bridge is a town in Carroll County, Maryland, United States. The population was 936 at the 2020 census.Much of the town was added to the National Register of Historic Places as the Union Bridge Historic District in 1994.

Union Bridge Historic District is a national historic district at Union Bridge, Carroll County, Maryland, United States. The district consists of this small piedmont village, which serves the area as a market center for the surrounding agricultural area. The greatest growth occurred in the 1880s after the Western Maryland Railway built its shops here.It was added to the National Register of Historic Places in 1994.

The Jacob Koons Farm is a historic farmstead at 1151 Otterdale Mill Road in rural Carroll County, Maryland, near Taneytown. The main farmhouse, a two-story rubble stone construction, was built in 1869. The property also includes several 19th century outbuildings, including a wood frame summer kitchen, a stone smokehouse, and a wooden barn.The farm was listed on the National Register of Historic Places in 2011.

Terra Rubra is a historic home and plantation located near Keysville, Carroll County, Maryland, United States. It was the birth site of Francis Scott Key in 1779. The present Federal-style house was built in the 1850s after the Key residence had become badly deteriorated. The original house was built in the 1770s by Francis Key for his son, John Ross Key, father of Francis Scott Key.It was listed on the National Register of Historic Places in 1978.

Pipe Creek Friends Meetinghouse is an historic Friends meeting house located at Union Bridge, Carroll County, Maryland, United States. It is a 1+1⁄2-story brick structure in Flemish bond on a stone foundation. The meetinghouse was begun in 1771 and completed the next year. A fire in October 1934 destroyed the interior, but the original benches were saved. The founders of the meetinghouse were immigrants from the north of Ireland. It was the Quaker meetinghouse attended by a great-grandfather of President Herbert Hoover.The Pipe Creek Friends Meetinghouse was listed on the National Register of Historic Places in 1976.

Hard Lodging is a historic home located at Union Bridge, Carroll County, Maryland, United States. It is built on a small cliff overlooking the site where its first owner, Solomon Shepherd, had a mill that is no longer standing. The house was built in three stages: the middle section, a 2+1⁄2-story brick structure, was probably built first; the main section of the house is attached to the west and is a Federal-style, three-by-two-bay, 2+1⁄2-story house with an interior gable-end chimney. Hard Lodging is currently a private residence and is no longer owned by the Historical Society. The home is an example of Pennsylvania German architecture. Hard Lodging was listed on the National Register of Historic Places in 1978.

Keysville is an unincorporated community in Carroll County, Maryland, United States. Terra Rubra was listed on the National Register of Historic Places in 1978.