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Posted on Jul 30, 2004 in War College

Custer’s Greatest Victory

By Bill Betson

For the Spring campaign Custer’s command had been reinforced from two to three brigades.  The 1st, Commanded by COL Alexander Pennington, consisted of the 1st Connecticut, 3d New Jersey, 2d New York, and the 2d Ohio Cavalry regiments, and a battalion of the 18th Pennsylvania.  The 2d, commanded by COL William Wells (acting for John Coppington) had the 8th, 15th, and 22d New York regiments, along with a squadron of the 3d Indiana, and a detachment of the 1st New Hampshire.  The new 3d Brigade, commanded by COL Henry Capehart, had the 1st New York (known as the "Lincoln" Cavalry), the 3d West Virginia, and elements of the 1st and 2d West Virginia.  Custer’s Division counted some 4,500 troopers at full strength.  All sporting distinctive red ties to mark them as a member of Custer’s Division, they were a proud bunch.


The march was miserable – only a soldier can know how miserable.  It was raining mixed with sleet most of the time, the roads were in horrible condition, and the streams and rivers were swollen.  On the second day, while swimming the North Fork of the Shenandoah in freezing weather, one soldier from the 1st Brigade drowned.  But despite the hardships, by all accounts the morale of Custer’s men was sky high.  They were well mounted, magnificently equipped, and confident they could whip anybody in their way.  They would quickly demonstrate that their confidence was well placed.

Having crossed the North Fork of the Shenandoah River on the 28th, the next day Custer’s men approached the Middle Fork near Mount Crawford and ran into the Rebels.  There waited Confederate General Thomas Rosser, one of the pantheon of southern cavalry heroes.  But Tom Rosser was also George Custer’s best friend.  Very close while at the academy, the two had already met many times on the battlefield, lately with the results going all George Custer’s way.  But on this day Rosser had perhaps 300 men, and could not stop the Union mounted force.  He could, however, delay the Yankees by burning the long wooden bridge over the river.  This he tried to do.

But Custer’s men had other ideas.  In an aggressive move that characterized Custer’s command, Henry Capehart had two of his regiments swim the river to strike at the Rebel flank.  Once they got across Capehart led the rest of his brigade in a mounted charge across the bridge.  They scattered Rosser’s men to the winds, put out the fire, and chased the fleeing Confederates to Staunton, which Sheridan’s entire force occupied later in the day.  This action would be a harbinger of things to come.  Meanwhile Early had withdrawn the remaining Confederate force east from Staunton along the railroad to Richmond, and taken up a defensive position along a ridge near Waynesboro.  He had told the citizens of Staunton before he left that Waynesboro was where he intended to fight.

Sheridan had now reached a decision point.  He could follow his orders and continue south to Lynchburg, or turn east and face Early.  Claiming (rather unconvincingly) that he could not leave Early behind him to continue to threaten the valley, Sheridan turned east and headed toward Waynesboro – and eventually Richmond. He directed Custer to take the lead and move out on March 2d to "ascertain something definite in regard to the position, movements, and strength of the enemy, and, if possible, to destroy the railroad bridge over the South River."  Custer would do more than that.

Although the Virginia Central Railroad headed east from Staunton through Waynesboro, no good roads did.  As they moved east, Custer’s men once again struggled through horribly muddy roads in a frigid downpour.  Custer reported that by the time his men had traveled a few miles, they were unrecognizably covered with mud.  Despite the weather Custer’s men quickly drove in the Rebel pickets when they reached them some six miles from Staunton.  Having driven the pickets 4-5 miles, Custer then came upon the prepared Confederate position at Waynesboro. 

At first glance the Confederate position appeared strong.  Placed on a hill in front of the Southern Branch of the Shenandoah River (see map), the fourteen (some sources say 11) cannon that Early had seemed to dominate all approaches. Thus, although the position was rather long for the amount of infantry in Wharton’s Division, the guns should have made up for that weakness.  Indeed, in the front near Richmond, this number of troops and guns would have seemed quite normal.  After probing the position with elements of Wells’ Brigade, Custer concluded that a direct frontal attack would result in prohibitive casualties.  Instead he began a careful reconnaissance of the position.

Waynesborough.  (Click to enlarge)

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