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October 21, 1861 Battle of Leesburg [CS]
Battle of Ball's Bluff [US]
Battle of Harrison Island [US]

General Nathan Evans [CS] defeats General Charles Stone [US]. Oregon Senator Edward Baker, field commander, becomes the first (and only) sitting senator to die in battle.
Virginia
  Battle of Ball's Bluff
  Civil War Firsts
October 21, 1863 Ulysses S. Grant leaves Bridgeport, AL to assume command of the troops in Chattanooga. The only road in a muddy wash with a horrible stench from the dead mules lying on either side. This was the road Rosecrans was using to supply his troops. Tennessee
  Ulysses S. Grant
  Battles for Chattanooga

Ongoing on this day:
June 15, 1864
April 2, 1865
Siege of Petersburg Virginia
  Robert E. Lee
  P. G. T. Beauregard
  Army of Northern Virginia
  Ulysses S. Grant
  Siege of Petersburg
April 12, 1861
May 10, 1865
The American Civil War
  The Civil War
October 19, 1862
October 23, 1862
Bragg moves south through the Cumberland Gap, essentially escaping the Army of the Ohio Tennessee
Kentucky
  Braxton Bragg
  Confederate Invasion of Kentucky
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