Washington Monument State Park

Zittlestown is an unincorporated community 2.2 miles (3.5 km) southeast of Boonsboro in Washington County, Maryland. It is situated on the western slope of South Mountain below Turner's Gap, along the historic National Pike, now designated U.S. Route 40 Alternate. Zittlestown is named after Michael Zittle, Sr. (1769-1850), who in 1811 purchased tracts of land there, and subdivided them.In the American Civil War, the Battle of South Mountain on 14 September 1862 was fought around Zittlestown.

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.

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.

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.

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.

Boonsboro is a town in Washington County, Maryland, United States, located at the foot of South Mountain. It nearly borders Frederick County and is proximate to the Antietam National Battlefield. The population was 3,779 at the 2020 census.

Boonsboro High School (BHS) is a public high school (grades 9 to 12) in Boonsboro, Washington County, Maryland, United States.

The JFK 50 Mile or the JFK 50 Mile Memorial is an ultramarathon that takes place annually in Washington County, Maryland, United States. The first race was held on 30 March 1963, one of numerous 50-mile (80 km) races that year. After the Kennedy assassination, many of these events were never held again. It is the oldest continuously held ultramarathon in the US.The current course records are held by Hayden Hawks (5:18:40) for men and Sarah Biehl (6:05:42) for women.The race starts in the town of Boonsboro, Maryland; the official starting line is marked by two commemorative bronze plaques, one on each side of Boonsboro's main street. It then heads east out of town toward the South Mountain Inn. The first 2.3 miles are on a hardball road, which leads to the Appalachian Trail. The Appalachian Trail piece is approximately 13 miles. The trail then continues on the Chesapeake and Ohio Canal for 26.3 miles, following the canal to Dam #4 on the Potomac River. The final leg of the Race follows 8.4 miles of hardball roads to Williamsport, Maryland. As of 2023, the race has a 13 hour time limit, runners that do not finish in 13 hours are required to withdraw from the race.The Race is held on the Saturday before Thanksgiving.The current race director is Mike Spinnler.

The Bowman House is a historic log house located at 323 North Main Street in Boonsboro, Maryland, and is locally significant as a typical example of those built in the area in the early 19th century.