Zittlestown, Maryland

The Battle of South Mountain, known in several early Southern accounts as the Battle of Boonsboro Gap, was fought on September 14, 1862, as part of the Maryland campaign of the American Civil War. Three pitched battles were fought for possession of three South Mountain passes: Crampton's, Turner's, and Fox's Gaps. Maj. Gen. George B. McClellan, commanding the Union Army of the Potomac, needed to pass through these gaps in his pursuit of Confederate General Robert E. Lee's precariously divided Army of Northern Virginia.Although the delay bought at South Mountain would allow him to reunite his army and forestall defeat in detail, Lee considered termination of the Maryland Campaign at nightfall.

Turner's Gap is a wind gap in the South Mountain Range of the Blue Ridge Mountains, located in Frederick County and Washington County, Maryland. The gap is traversed by U.S. Route 40 Alternate, the old National Pike. The Appalachian Trail also crosses the gap along the ridgeline.

The Turner's and Fox's Gaps Historic District comprises the Civil War-era battlefield involved in the Battle of South Mountain, which took place on September 14, 1862. The district extends on the west to the slopes of South Mountain in the area of Zittlestown, and to the east beyond the foot of the mountain to the small community of Bolivar. The district is characterized by steep mountain terrain in the west and open farmland in the east, with Turner's Gap to the north and Fox's Gap to the south. The district includes 115 contributing buildings and structures. The most significant contributing buildings are the Mountain House Inn (now the Old South Mountain Inn) and the White House Inn, or Beachley House. Also included in the list is the Reno Monument at Fox's Gap, shown at right. The Old National Pike, now known as U.S. 40 Alternate, passes over South Mountain at Turner's Gap.The district was placed on the National Register of Historic Places on January 12, 2011.

Dahlgren Chapel is located at the summit of Turner's Gap in western Maryland between Middletown and Boonsboro. The Gothic revival stone chapel was built in 1881 and consecrated as the Chapel of St. Joseph of the Sacred Heart of Jesus. Most of the building materials came from the immediate area of the site, while a marble altar was imported from Italy. The chapel was built for Sarah Madeleine Vinton Dahlgren, daughter of Congressman Samuel Finley Vinton, who had married Admiral John A. Dahlgren, inventor of the Dahlgren gun, in 1865. Admiral Dahlgren died in 1870. Mrs. Dahlgren purchased a former tavern on South Mountain at Turner's Gap as a summer retreat, naming it Dahlgren Manor. The chapel was built across the National Road from the house. When Mrs. Dahlgren died in 1898, she was interred in the chapel's family crypt. After a period under the ownership of the Sisters of the Holy Cross from 1922 to 1925 the chapel returned to the Dahlgren family. It was purchased in 1960 by Richard G. Griffin, who undertook a restoration. The property was acquired by the Central Maryland Heritage League in 1996. The chapel is included in the Turner's and Fox's Gaps Historic District, but as a non-contributing structure, owing to its post-Civil War construction, which places it outside the historic district's time of historic emphasis.

Washington Monument State Park is a public recreation area located approximately one mile (1.6 km) southeast of Boonsboro, Maryland. The park preserves the Washington Monument, a 40-foot-tall (12 m) tower honoring George Washington, the first President of the United States. The monument sits along the Appalachian Trail near the summit of South Mountain's Monument Knob. It was added to the National Register of Historic Places in 1972. The park is managed by the Maryland Department of Natural Resources.

Fox's Gap, also known as Fox Gap, is a wind gap in the South Mountain Range of the Blue Ridge Mountains, located in Frederick County and Washington County, Maryland. The gap is traversed by Reno Monument Road. The Appalachian Trail also crosses the gap along the ridgeline.

Appletown is an unincorporated community in Washington County, Maryland, United States. Appletown is located along Maryland Route 67, 1.8 miles (2.9 km) south of Boonsboro.

The Rocky Run shelter(s) are backcountry shelters located on the Appalachian Trail near Boonsboro, Maryland. They are situated next to the Rocky Run spring and a steep hill side. The original Rocky Run shelter sleeps six people, has a flat floor, and provides enough space to sit up. The new shelter can sleep up to sixteen and features a wood floor and a plywood-floored loft, as well as a covered front deck and large windows which flood the shelter with light. Accommodations available include two decks, a grill pit, porch swing, and semi-enclosed privy.

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.

The Routzahn-Miller Farmstead is a historic home and farm complex located at Middletown, Frederick County, Maryland, United States. It consists of a Federal style-influenced brick house and smokehouse, both built about 1825; a later frame out-kitchen / washhouse; a standard Pennsylvania barn; a 20th-century dairy barn and milk house; and a 20th-century equipment shed. The Pennsylvania barn was probably built in the late 19th century and was recently rehabilitated for use as a preschool. The complex is located on a 16.7-acre (68,000 m2) parcel on the east flank of South Mountain. It is representative example of a type of domestic and agricultural grouping which characterized the rural mid-Maryland region from the early 19th century through World War II era.The Routzahn-Miller Farmstead was listed on the National Register of Historic Places in 2006.

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.

Boonsboro Historic District is a national historic district at Boonsboro, Washington County, Maryland, United States. The district includes 562 contributing elements. Its component buildings chronicle the town's development from its founding in 1792 through the mid 20th century. Most of the late 18th and early 19th century development in Boonsboro occurred along Main Street, then part of a principal market road between Williamsport, Hagerstown, Frederick, and Baltimore, Maryland. They are mainly of log, frame, or brick construction, with a few stone buildings interspersed. The majority of the buildings in the district date from the 1820-1850 period coinciding with peak use years of the National Road. Other features of the district include the Boonsboro Cemetery laid out about 1855 in a 19th-century curving plan with a number of exceptionally artistic gravestones, and the office/depot of the Hagerstown-Boonsboro Electric Railway. The period of significance, from 1792 to 1959 tracks the continuous growth and evolution of the town through the date by which the district had substantially achieved its current form and appearance.It was added to the National Register of Historic Places in 2005.