The 1,300 acre plantation was almost a village in itself, with a smokehouse, kitchen garden, laundry, dairy, pigpen, springhouse, barns, sheds, stables, a blacksmith shop, stockyard, farm manager’s home, quarters for 25 slaves, and a schoolhouse. Col. Hamilton Rogers built the home in 1830. Four of his sons enlisted in the Confederate Army and served with distinction; one son was killed at the battle of Spotsylvania Courthouse, and a nephew rode with Mosby’s Rangers, and Rogers’ brother Asa was a general in the Confederate Army. All told, at least 12 Rogers men served the Confederacy. One evening in December of 1862, Hamilton and Mary Rogers entertained Gen. J.E.B. Stuart and his officers. It is said that a dashing young officer of the Confederacy asked Gen. Stuart permission that night to form a group of Rangers. His goal was to impede Union food and munitions shipments by using guerrilla tactics and the element of surprise. Some academians believe it was the first time in military history that such tactics became an accepted part of military strategy. The young officer was John Singleton Mosby, after whom the highway that runs by the front door of Oakham Plantation is named. He was a Virginian by birth and attorney by profession, and became known as the Grey Ghost of the Confederacy.
Oakham stands apart from other plantations because unlike most old Middleburg properties that have been divided, subdivided, sold, and re-sold, it is still owned by the great-great-grandsons of Col. Hamilton Rogers.