Banks had made it to Winchester and was headquartered in George Seevers home where he was informed that Confederate troops were marching on Winchester from Front Royal. Federal troops had been marching into the city since 5:00 PM. He sent a dispatch to President Lincoln at 8:00 PM informing him that he was facing the combined forces of Jackson and Ewell. He also told them he arrived with all of his wagons when in reality he had lost a little over 100. Banks would need to organize his force in a hurry. The 10th ME Infantry and a few isolated cavalry squadrons were the only troops in town. Colonel George Beal of the 10th ME had sent companies C and I and the 1st MI Cavalry under Major Charles Town to patrol the road from Front Royal. They encountered Ewell’s force 4 miles from town. A courier arrived with a dispatch from Jackson ordering Ewell to join him at Newtown (modern day Stephens City). Ewell ignored the order considering it outdated. He ordered William Kirland of the 21st NC to drive back the small Federal force in their front. Ewell continued to within 2 miles of Winchester where he decided to stop for the night.

Jackson moved into Newtown after the Union rearguard abandoned it. Major Wilder Dwight of the 2nd MA was now in charge of the Federal rearguard that consisted of only three companies, a total of about 150 men, with orders to delay Jackson as long as possible. Just north of Newtown on the Valley Pike he set a trap for Ashby’s Cavalry and drove them back. Jackson realigned his column placing artillery behind the cavalry followed by the Stonewall Brigade. As they advanced toward Bartonsville skirmishers were sent out from the 33rd VA under Colonel John Neff. A sharp fire fight erupted with the 2nd MA losing 20 men and Neff eight. When Jackson ordered the 7th VA Cavalry to charge, a volley by Dwight’s men sent them fleeing toward the rear crashing into cavalry and infantry injuring several of their own men. Jackson watched in disgust at their undisciplined response under Colonel Ashby. Having lost 17 men killed and 3 wounded Dwight withdrew his small force from Bartonsville. General Winder, commander of the Stonewall Brigade, ordered the 2nd (Colonel James Allen) and 27th VA (Colonel Andrew Jackson Grigsby) to clear out Bartonsville. By midnight the Confederates controlled the town and were now three miles from Winchester. Here Jackson again readjusted his column calling forward Companies A and K of the 5th VA under Lieutenant George Kurtz. He did this because these men were local to the Winchester area and would be moving forward in the dark as skirmishers. On the outskirts of Kernstown they once again ran into pickets from the 2nd MA. The Massachusetts men were using the nearby home of Joseph Mahaney, the only house in the area, to care for their wounded. They were forced to leave the wounded and their physician behind as they pulled back to Winchester.

Dwight and his 150 men of the 2nd MA had slowed Jackson to the extent that it took him 6 hours to travel the last six miles. Colonel Gordon and Dwight then traveled to the Seevers house along with a Confederate prisoner, a surgeon captured at Newtown, to update General Banks. Gordon and Dwight reported that they were vastly outnumbered by Jackson’s army and that he would attack in the morning, advocating for a retreat toward the Potomac. Banks listened to the men but did not discuss his plans with them. Dissatisfied Gordon then rode to the Taylor Hotel downtown and woke Generals Alpheus Williams, Samuel Crawford and George Greene to advocate for a retreat. It was now 3:00 AM and having a somewhat clearer picture of what he was facing Banks began to set his wagon train in motion from the fairgrounds north of Winchester toward the Potomac, but he would need to buy them time to escape.

Having spent several months in Winchester he knew the terrain and road system well. Rebel infantry could only attack him from the south and he had control of the high ground there. Infantry and artillery placed on the hills would make it difficult for Jackson to advance and allow Banks to view for himself the size of the Confederate force he was facing. Banks knew that he had only eight infantry regiments, less than 4500 men, most with very little combat experience. He would also need time to organize his roughly 1,000 cavalrymen, 300 of which were casualties during the previous day’s actions, who were scattered across town looking for forage for their horses. He only had two artillery batteries a total of 12 cannon, half of which were rifled. From War Department telegrams he knew that five regiments were on the road from Harper’s Ferry and that Frémont was headed to the Shenandoah Valley. Banks wanted to buy more time to evacuate the city and to test the size of Jackson’s force.

Stonewall Jackson was only one mile away from Winchester when he and his men halted at 2:30 AM. He had driven back pickets from the 1st MD (US) Cavalry at Hillman’s Tollgate and was at Abraham’s Creek. Jackson wanted to strike as quickly as possible before Banks could reorganize and dig in on the high ground. He especially wanted to occupy Bowers Hill a ridge on the west side of the city. Jackson, a former artillery instructor, knew that if he could get his guns there, they could suppress the fire of any Federal artillery battery. Little did Jackson know that at 2:30 AM it was defended by only one company of the 29th PA Infantry and a cavalry camp. What Jackson wanted and what his exhausted army and cavalry could provide were two completely different things. Most of his infantry had marched for 14 straight hours with no rations, and the Confederate wagon trains were miles away. An officer reported to him that during the march many of his men had stumbled off the road and fallen asleep. Jackson decided to allow his men to rest for a short period. There may have been other factors that played a role in his decision. The unusually large size of Banks’ wagon train may have suggested to him that the force he was facing was much larger than it actually was and there was no way to determine that in the dark. At 3:00 AM Jackson called up Colonel Stapleton Crutchfield and instructed him to deliver a written order to General Ewell to cross over to Newtown and head to Strasburg to deal with the Union force there to protect the tail of the army. It would take Crutchfield several hours to reach Ewell via the circuitous route he took. He would ride over 20 miles to reach Ewell who was only about a mile and a half away as the crow flies.

By 4:00 AM two sections of Union Lieutenant J. Presley Fleming’s Hampton’s battery arrived in town with an additional 16 cannons, 10 of which were rifled. Banks left the troop deployments on the high ground that overlooked the southern approach to the city to Brigadier General Alpheus Williams. Williams first made sure the supply wagons were on the road to Martinsburg before he headed south to aid his subordinates in placing the troops. Colonel Gordon had begun deploying his 2100 men on the west side of the Valley Pike about 200 yards south of town. He sent two companies of the 29th PA to a knoll about 600 yards further south on the north side of Abraham’s Creek. Four hundred yards southeast of Gordon’s left flank, Colonel Dudley Donnelly’s brigade was on both sides of the road into southeast Winchester at the junction of the Front Royal-Winchester Pike and the Millwood Pike. Six smoothbore cannons from Battery F of the 4th US Light Artillery commanded by Lieutenant Franklin Crosby were deployed at 4:00 AM on Camp Hill covering Ewell’s approach into town. Jackson allowed his men a 90-minute rest and started forward at 4:00 AM. His objective was Bowers Hill. The Stonewall Brigade under General Winder advanced to Hollingsworth Mill (see map below) with orders from Jackson that “You must occupy that hill.” The battle would begin shortly.

Next- The First Battle of Winchester- May 25, 1862

Sources

Three Days in the Shenandoah Stonewall Jackson at Front Royal and Winchester by Gary Ecelbarger

Stonewall Jackson’s Valley Campaign Shenandoah 1862 by Peter Cozzens

The Official Records of the War of the Rebellion Chapter 24 pages 536-645