Culpeper County occupied a strategic location between the Rappahannock River to the north and the Rapidan River to the south.  Through the county ran the important Orange Alexandria railroad (now Southern Railroad).  The country side along this rail line was witness to numerous armed engagements throughout the Civil War.  The two most important battles fought in Culpeper County were Cedar Mountain (August 1862), and Brandy Station (June 1863) which was the largest Cavalry battle ever fought in North America.

The County was occupied by armies of both the North and the South at various times.  It was headquarters to Union General John Pope in 1862, then Robert E. Lee in 1863, just prior to the Gettysburg Campaign, and finally in the winter of 1863-1864 was headquarters to General George Meade and later Ulysses S. Grant, when over 100,000 Union troops made it their winter encampment prior to the Wilderness Campaign in the spring of 1864.

It was during these years that Rose Hill and the Ashby family was witness to many of these events.  Battle damage is today still visible in the attic and front porch of the main house.  It is unclear exactly when this damage occurred, but a significant series of Cavalry engagements took place in the vicinity on September 13th 1863.  During the action Confederate forces of the 11th Virginia Cavalry commanded by Col. Lunsford Lomax and supported by Col. R. L. T. Beall’s 9th Virginia Cavalry, were pushed back west by Union forces under General Judson Kilpatrick and George Armstrong Custer.

In 1938 newspaper article about Rose Hill suggests that the house was shelled by a Federal battery hoping to get at Confederate soldiers hidden in a “holly planting” just to the west of the main house.

Shortly thereafter Rose Hill was made the winter Headquarters of the Third Division U.S Cavalry under Brig. General Hugh Judson Kilpatrick.  Stories passed down through the years recount some of the experiences of the occupation.

Before the Union troops arrived the family was worried that they would be stripped of food and so hid numerous hams underneath a large dining room table, which they then covered with wooden slats.  The family was forced to move into the basement while General Kilpatrick and his staff requisitioned the more comfortable upper stories of the house.  Many times the family heard the soldiers complain of how heavy “that table” was as they moved it around never realizing what was hidden underneath.

Don and John’s Grandfather John Austin recalled from his parents that General Kilpatrick treated the family with courtesy and kindness even supplying them with food from his own table on occasion.  This is at variance, however with a late post war letter dated (1902) from a Capt. Aaron Levy of the U.S Signal Corps who was also stationed at Rose Hill during the occupation.  In that letter he offers apologies to Miss. Ashby for the poor treatment which he felt they endured under general Kilpatrick, including being denied food at one point.

It was during this time at Rose Hill that plans were made for General Kilpatrick and his second in command Col. Ulrich Dahlgren to launch a Cavalry raid on Richmond.  The ambitious and ill fated plan was to free the Union prisoners of war impounded on Belle Isle in the James River and in Libby Prison at Richmond.  They also planned to possibly capture and kill members of the Confederate government of Jefferson Davis.

During that time of occupation and planning, many Washington notables including Senators and Vice President Hannibal Hamlin were entertained as guests of General Kilpatrick at Rose Hill.  There is an amusing account of some of the escapades surrounding the social activities at Rose Hill which are detailed in Virgil Carrington Jones book Eight Hours Before Richmond.

It was later in the War after the occupying Union forces had vacated the home that a young Confederate of the 9th Virginia Cavalry rode up to the house to ask for food.  Young Mary Jane Ashby had just baked some fresh biscuits and had dumped them “hot” into Thomas Rosser Covington’s haversack.  He later returned after the War to woo and marry Miss. Ashby in 1868 and raise a family at Rose Hill.

It can be noted that Col. Dahlgren’s part of the ill fated Richmond raid met with disaster when he was killed near King William Court House ambushed by the 9th Virginia Cavalry.