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The land at Keswick Vineyards was part of the original 1727 Nicholas Meriwether Crown Grant that comprised nearly 18,000 acres on the east side of the Southwest Mountains. George Barclay Rives, a direct descendent of the original grantee, built the current residence in 1911 and named it Edgewood Estate.

The property was the site of two important historical events: one during the Revolutionary War and the other during the Civil War. On June 4, 1781, Captain Jack Jouett rode 40 miles through the night to warn then-Virginia Governor Thomas Jefferson and the Virginia Legislature of the approach of British troops led by Colonel Banastre Tarleton.

Tarleton's troops arrived at Castle Hill, the original tract of land to which Edgewood Estate belonged, just after dawn on June 4, 1781. Legend has it that Tarleton and his troops stayed for breakfast, thus delaying their march to Charlottesville, allowing for Jefferson and others to escape. 

Almost one hundred years later, Edgewood Estate became a stopping point during another American War. Confederate General James A. Longstreet was ordered to move his troops from East Tennessee on April 7, 1864, to Charlottesville to prepare for the Battle of the Wilderness. The Confederates detrained at Charlottesville and were then marched to various campsites, including Edgewood Estate. Historians believe that just days before the movement toward the Wilderness, Longstreet's men were reviewed by General Robert E. Lee.