The Kennedy Farm served as abolitionist John Brown's headquarters as he planned his October 1859 raid on Harpers Ferry. The farmhouse was originally built by Robert F. Kennedy in the 1850s and sat empty after his death in the spring of 1859. John Brown and his followers arrived in the area on July 3, 1859. Looking for a place to stage their upcoming raid on nearby Harpers Ferry, they presented themselves as cattlemen from New York who were looking for property. A local resident suggested the now-vacant Kennedy farm and Brown and his men leased the property and spent a total of three and a half months in the Kennedy Farmhouse. Today, the farmhouse has been entirely restored by area preservationists with the support of state and federal funds. The Kennedy Farm was designated as a National Historic Landmark and is also on the National Register of Historic Places.

John Brown's Fort was a U.S. Armory engine and guard-house constructed for the Musket Factory in 1847-8. It's original location was across the street where the John Brown monument now stands. In 1859, John Brown and his men used this fort to attempt to free the slaves of the area, his attempt was unsuccessful but brought national attention to the area of Harpers Ferry and raised tensions around the topic of slavery. The Engine House was repositioned here in 1968 and restored in 1976-7,

The Allstadt House and Ordinary, or tavern, property was originally built in 1790 by the Lees family. In 1811, 114 acres of the property was sold to Jacob Allstadt, who then obtained a license to run an ordinary on the site. The house was renovated and enlarged in the 1830s. The property's main claim to fame is its part in the John Brown Raid on October 16, 1859, where John Cook, one of John Brown's men, took John Allstadt, his 18 year old son John Thomas, and seven of their slaves as hostage along with the Washington's from the nearby Beallair estate.

Beallair, or Beall-Air as it is sometimes written, was the home of Lewis William Washington, the great-grand-nephew of President George Washington. When Lewis William Washington inherited the property in 1827, he incorporated an old stone house into the taller, front portion he had built between 1850 and 1855. As it stands today, Beallair is a two story stuccoed brick structure with a stone foundation and boasting a classical revival architectural style. Aside from its impressive architectural features and state of preservation, Beallair played a part in John Brown's Raid of Harpers Ferry on October 16, 1859 when Lewis William Washington was kidnapped and held hostage by Brown and his men. Beallair was added to the National Register of Historic Places in 1973.

The Jefferson County Museum is located in historic downtown Charles Town and shares a building with its partner organization, the Charles Town Library. Since its founding in 1965, the museum has been dedicated to fostering the understanding and love of history. The museum is committed to the acquisition, preservation, and exhibition of artifacts and documents of historical value and relevance to the county and the region from early Native American activities and the European colonization in the 1700s through the 21st century war on terrorism.

The Jefferson County Courthouse was originally built between 1803-1808 in Charles Town on a plot of land donated by Charles Washington. It was replaced by a larger structure in 1836. Due to damage incurred during the Civil War, the Jefferson County seat was temporarily moved to Shepherdstown, and then moved back to Charles Town in 1872. The Jefferson County Courthouse is famous for housing two treason trials: John Brown's trial after his raid on the Harpers Ferry armory in 1859, and the trial against unionizing coal miners from Logan County in 1922. Today the courthouse remains in operation and is open to the public. It was added to the National Register of Historic Places in 1973.

Though it was torn down in 1919, the old Charles Town jail was where John Brown was held before his hanging, sitting diagonally across from the courthouse. John Brown was taken by Robert E. Lee and his men on October 17, 1859 and transported to the jail while awaiting trial. He remained there until his hanging on December 2, 1859. In it's spot now stands the Charles Town post office.

Built in 1891, the Gibson-Todd house was designed by the architect Thomas A. Mullet. While the building has gotten attention over the years, the site is better known for being the place where John Brown was hanged following his trial. John Thomas Gibson was the first occupant of the house after it was completed. His granddaughter, Frances Prakette, married Augustine J. Todd and donated the house to the National Trust for Historic Preservation. The house is now privately owned.