Foiling the Trap
After the Battle of Antietam in September 1862, Gen. Robert E. Lee's Army of Northern Virginia escaped to Virginia. President Abraham Lincoln repeatedly urged Union Gen. George B. McClellan to pursue and attack. Following a plan that Lincoln devised to trap Lee's army in the Shenandoah Valley, McClellan finally got his Army of the Potomac moving. On November 1, Union cavalry Gen. Alfred Pleasonton began leading the advance from Philomont toward Upperville. Gen. J.E.B. Stuart's cavalry delayed him for three days. On November 5, learning that Lee's army had evaded the trap and reached Culpeper County, Lincoln ordered McClellan relieved of command.
On Monday, November 3, 1862, Confederate Gen. J.E.B. Stuart's 900 troopers and 12 guns were stretched thinly over a two-mile-long line across the fields in front of you. Beyond Stuart's line, Union Gen. Alfred Pleasonton, with 4,000 men and 18 guns, approached from the north. As Stuart described the scene, "About 9 A.M. the enemy advanced on our new position with cavalry, infantry and artillery, moving simultaneously by all the roads and fords."
Stuart's line held tenaciously almost all day but was finally breached by a successful infantry attack on his right flank. He and his men, pursued by Union cavalry, retreated in a wild gallop across the fields just in front of you and along Ashby's Gap Turnpike through Upperville to your left. As they approached Ashby's Gap, Confederate cannon fire from there halted the Federals, and Stuart's men found safety. Although the three days of fighting ended in Stuart's retreat, he had accomplished his mission. The advance of Lee's army reached Culpeper County the same day to block any Union march on Richmond. Lincoln's plan was foiled. Two days later, he ordered McClellan relieved and replaced with Gen. Ambrose E. Burnside.
The next year, as Lee marched through the Shenandoah Valley to invade Pennsylvania, Stuart and Pleasonton fought again here. Once more, Stuart successfully screened Lee's army from Pleasonton's cavalry.
Ida Dulany watched the day's action from Oakley Plantation, about half a mile to your right. She wrote in her diary, "We could see from the location of the batteries that they approached us. ... Soon there were no more Southerners in sight and the house was surrounded by Yankees. ... We watched the battery pouring out shells against our battery which was in the vineyard. ... The shells from both batteries burst in full sight of us.