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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.

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.

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.

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.

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.

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.

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.