During the Civil War, Urbanna was occupied at different times by Federal and Confederate forces as ships came and went into Urbanna Creek. On November 8, 1861, just off the mouth of the creek, a Union tug and steamer armed with cannons fired upon the town while the Middlesex Light Dragoons, later part of the Confederate 55th Virginia Infantry, were using the old County Courthouse building as barracks. As the shelling began, soldiers and residents fled from homes and buildings into the Lansdowne ravine behind Virginia Street and the Spouts Cove ravine on Watling Street, and although homes and the courthouse were struck during several hours of fire, legend says the only death from cannon fire that day was a town hare. Union vessels also offered a path to freedom for the town's large enslaved population, and when word spread that ships were on Urbanna Creek, freedom seekers hid in town ravines at night and at daylight walked down Watling, Virginia, Cross, or Prince George streets to Union sailors; several later enlisted in the Union Army, served in the 36th U.S. Colored Infantry, and were among Union forces that invaded Middlesex in 1861. Major General George B. McClellan also proposed to President Abraham Lincoln the Urbanna Plan, a military plan to move Union forces behind Confederate flanks and invade Richmond through Urbanna, but just before the town's invasion in March 1862, Confederate forces moved from Manassas toward the Rappahannock River, making the plan strategically useless.