Background
After the Battle of Fort Stevens on July 11, a Union column, consisting of the VI Corps and elements of the XIX Corps under Maj. Gen. Horatio G. Wright, pursued Lt. Gen. Jubal Early's Army of the Valley as it withdrew from the environs of Washington, D.C., through Loudoun County, Virginia. On July 15, Wright's force was joined by elements of Brig. Gen. George Crook's command, which had accompanied Maj. Gen. David Hunter during his retreat through West Virginia following the Battle of Lynchburg on June 18.
After two brief engagements in Loudoun County at Heaton's Crossroads (present day Purcellville) and Woodgrove on July 16, Early's main force crossed the Blue Ridge Mountains at Snickers Gap and established themselves around Berryville. To cover his rear, Early left substantial rearguard forces at main river crossings of the Shenandoah River. On July 17, the Union cavalry passed through Snickers Gap and unsuccessfully attempted to force passage of the river at Castleman's Ferry (Snicker's Ford).
The following day, Gens. Crook and Wright arrived at Snickers Gap and determined to attack what they mistakenly thought was a light picket line of Confederates along the river, left to cover Early's retreat up the Valley. Instead of allowing his cavalry to cross the river and reconnoiter the Confederate positions to confirm this assumption, it was dispatched to Ashby's Gap to attack Early's supply train which was traveling to the south of Early's main army. Wright then developed a plan where a small Federal force would cross the river downstream from the main crossing at Castleman's Ferry and flank the Confederate position. Gen. Crook assigned Col. Joseph Thoburn to this task.
Read more about this topic: Battle Of Cool Spring
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