Timeline of Civil War Events in the Winchester Area



May 23

The State of Virginia ratifies the Articles of Secession from the United States.

June 1

Joseph Johnston evacuates Harpers Ferry and pulls his Army of the Valley back to Winchester. Winchester becomes the front line of the Confederacy.

July 18

Johnston marches his Valley Army from Winchester to reinforce Beauregard at Manassas, leaving a small force of militia behind to defend the town. But Union forces under Patterson withdraw across the Potomac, leaving Winchester in Confederate hands.


November 4

Thomas 'Stonewall' Jackson is assigned to the command of the Valley District, with headquarters at Winchester.

March 11

Jackson evacuates Winchester in the face of superior Union forces.

March 12

Union troops under Nathaniel Banks occupy Winchester for the first time.

March 23

First Battle of Kernstown

Thomas Jackson (4,000) vs. Nathan Kimball (9,000)

Jackson responds to intelligence that most Union troops have left the city by attacking what he hoped was a small rearguard. His information was wrong. Jackson's only defeat while in command of an army forces him to retreat back up the Valley. (Note: "up the Valley'' in the Shenandoah means south, as the Valley gets higher in elevation the farter south you go.)

May 25

First Battle of Winchester

Thomas Jackson (16,000) vs. Nathaniel Banks (6,500)
In a surprise move, Jackson returns north via the Luray Valley, overrunning Front Royal and almost getting behind Banks' army at Strasburg. Banks fights a brief delaying action on the south side of Winchester before fleeing across the Potomac, and Confederate forces reoccupy Winchester.

May 30

Jackson heads back up the Valley, barely escaping being trapped between Shields’ and Fremont’s pursuing armies.

June 4

Winchester is reoccupied by the Federals

September 2

As Jackson descends on Harpers Ferry from the northwest Union forces under Julius White evacuate Winchester (only to be surrendered at Harpers Ferry). Confederate troops return to Winchester, which becomes the supply point for Lee’s Army at the Battle of Sharpsburg (Antietam)

Late September

Winchester becomes a major hospital for the wounded after Sharpsburg. Jackson's Second Corps goes into camp around the town.

November 22

Jackson leaves Winchester to join Lee on the Rappahannock, leaving behind a token force under “Grumble” Jones. Jackson will never return to Winchester.

December 3

Union forces under John Geary briefly occupy Winchester. He withdraws after only a few hours due to a smallpox epidemic.

December 4

Jones' cavalry reoccupies Winchester

December 13

Jones moves south to Strasburg, leaving Winchester unoccupied.

December 24

Union forces reoccupy Winchester.


January 1

Robert Milroy’s Union division moves into Winchester. Milroy, a fervent abolitionist, takes command of the Lower Valley and opresses the pro-Confederate population.

June 13 - 14

Second Battle of Winchester

Richard Ewell (12,500) vs. Robert Milroy (7,000)

As part of Lee's Gettysburg Campaign, the Second Corps, under Richard Ewell since the death of Jackson, are to clear Union forces out of the Shenandoah Valley and advance into Pennsylvania in advance of the main army. When Ewell arrives Milroy decides to fight it out. Ewell flanks and takes several important Union positions. Milroy decides to retreat after dark on the 14th.

June 15

Milroy runs into a blocking Confederate force a short distance outside of town at Stephenson's Depot just before dawn on the 15th. His army is annihilated and mostly captured in a night battle. Confederate once again return to Winchester.

July 22-24

After his defeat at Gettysburg, Lee retreats up the Shenandoah Valley. Winchester is reoccupied by the Federals.


July 1

Jubal Early’s Confederates sweep through Winchester on their way to Washington D.C.

July 20

Battle of Rutherford Farm

Stephen Ramseur (3,300) vs. William Averell (2,350)
Ramseur tries to turn back Federal forces moving south but is thrown back. The Federals push south through Winchester after the battle and take a position on the high groundaround Kernstown.

July 24

Second Battle of Kernstown

Jubal Early (14,000) vs. George Crook (10,000)
Federal Forces are thrown out of Winchester.

September 19

Battle of Opequon, or Third Battle of Winchester

Jubal Early (12,000) vs Philip Sheridan (40,000).

After the largest and costliest battle in the Shenandoah Valley during the Civil War, Confederate troops evacuate Winchester for the last time.

About the Author • ©2007-2014 Steve Hawks