At 6:00 AM on the 25th Jackson had his men on the move north toward Winchester on the Front Royal- Winchester Road. Within 2 hours the head of the column had reached Nineveh six miles north of Front Royal. He was now only 13 miles from Winchester which at that time was defended by only about 900 Yankees. Jackson was proceeding cautiously because his chief engineer, Lieutenant Boswell, who he had sent days earlier to Signal Knob to determine the size of Banks’ force, reported that Banks had 12,000 men under his command. In reality he only had 6,000. In addition, it was possible that Banks could be reinforced from Harper’s Ferry. Jackson knew Banks could react to the news at Front Royal in one of three ways. He could stay where he was in Strasburg (unlikely), head east along the Manassas Gap Railroad to Washington (possible), or most likely head north toward Winchester and Harper’s Ferry (most likely), but he wanted to be prepared for any of those options. He needed to know which way Banks was headed. Surprisingly, Jackson had sent no one to reconnoiter down any of the three roads leading to the Valley Pike nor to Signal Knob. At 8:00 AM the front of Banks’ wagon train was at Newtown (modern day Stephens City) and the end of the train was still in Strasburg. Banks’ entire army would not leave until the last wagon cleared town (9:00 AM). At Nineveh an old colonial period road, the Richmond Road, ran six miles northwest to Newtown, shown on the map below. Jackson ordered Brigadier General George Steuart to take 300 men from the 2nd and 6th VA to Newtown and observe any possible Union movement at the intersection with the Valley Pike.

Jackson moved his army three miles further north to the Double Tollgate (the intersection with the Millwood-Newtown Pike) and decided to halt until he had further news of Banks’ movements. Jackson and his staff rode back about 1.5 miles to the home of Dr. Mason and had breakfast. After breakfast Jackson rode back south with his cartographer Jed Hotchkiss to Cedarville. At 10:00 AM Steuart and his cavalry reached the intersection with the Valley Pike. For as far as he could see in both directions the pike was lined with Banks’ wagons. There was no longer any question as to which direction the Federals were headed, and he sent a courier back to notify Jackson. Until infantry support could arrive, Steuart decided to attack and slow down the wagon train. They hit the column right in the section where ambulances were transporting the sick and wounded. Two hundred unarmed men were captured and one, Daniel Derrickson, from Company B of the 66th OH was killed. The wagons behind the ambulances were driven by black teamsters who feared that they would be killed if captured, as a result they fled. Some attempted to turn their wagons around and tipped them over, completely blocking the road. The 1st MI Cavalry under Major Angelo Paldi charged north from Middletown to meet the threat. The Union 1st MD Cavalry riding south from Winchester under Colonel Charles Wetschky also encountered the Rebels who fell back into the woods east of the turnpike and sent another courier back to Jackson to request infantry and more cavalry support.

At 10:15 AM Union Colonel Dudley Donnelly’s brigade was marching through Middletown as the wagon panic reached that town. Ordering the wagons to clear the roads his men marched north on the double quick. Just north of town he spotted Steuart’s men in the woods. Two companies of skirmishers drove the Confederates back. The wagon panic reached back to Banks at Cedar Creek where he ordered his troops to the front and the wagons to the rear. Disabled wagons were burned. Banks also sent orders back to Captain James Abert in Strasburg to instruct Collis’ Zouaves to move forward and guard the Cedar Creek bridge in the event that the army needed to fall back to Strasburg and be prepared to burn it if necessary.

Jackson was still in Cedarville with Jed Hotchkiss, Major Dabney and Lieutenant Boswell. At 11:00 AM Jackson ordered Hotchkiss to take 16 cavalrymen from the 7th VA and proceed west down the Chapel Road (modern day Reliance Road- Route 627) and find Banks, sending couriers back to him every 30 minutes. Fifteen minutes later the first of Steuart’s couriers found Jackson. Jackson now knew Banks was heading to Winchester. Jackson sent orders off to Ewell telling him to prepare to move and await further orders as to where and to detail the job of guarding the Federal prisoners to the infantry in order to free up the cavalry that had been guarding them. Jackson appears to have forgotten that the prisoners were not at the head of the column with Ewell but were in Front Royal. The order would have to travel to the front of the column and then all the way back to the rear only a couple of miles from where Jackson was at the time. Hotchkiss in the meantime quickly ran into Union cavalry on the Chapel Road and requested reinforcements. He was opposed by five companies of the 1st ME Cavalry (Lieutenant Colonel Calvin Douty) and 2 companies of the 1st VT Cavalry (Major William Collins). Jackson quickly sent Company H of the 7th LA in support.

Not knowing the size of the force at Winchester Jackson decided to attack Banks’ column along the Chapel Road with the remaining companies of the 7th VA Cavalry, Poague’s Rockbridge Artillery, Chew’s Horse Artillery, General Taylor’s LA Brigade and the Stonewall Brigade. Colonel Turner Ashby would lead the advance, and the Stonewall Brigade would take up position behind the Louisianans. The Federals seeing the size of the force headed toward them withdrew toward Middletown. At 3:15 PM one mile from town Colonel Ashby sent Major Oliver Funsten with 100 cavalrymen north via a backroad to strike the pike between Middletown and Newtown. The Federals arrived in Middletown at 3:30 PM. Upon arriving in town Lieutenant Colonel Douty learned that Banks and the Union army had already passed through several hours ago. He also learned that General Hatch and the rearguard had just left Strasburg. Douty decided to wait for him. As the Confederate artillery opened fire General Hatch arrived with 6 companies of the 5th NY Cavalry. They would try and escape through the streets of town as a unified command. Ashby had disrupted the column of wagons on the pike at the northern end of town blocking the road and Major Funsten had struck the Valley Pike one mile north of town. A stone wall lined the eastern side of the Valley Pike at a bend in the road. The LA infantry took up position behind the wall near the bend. Crutchfield placed his cannons on the west side of Riding’s graveyard a hundred yards from the pike. Chew’s guns fired on the Federals from about a half mile away killing Major Cilley of the 1st ME Cavalry severing his arm at the shoulder. The Federals started forward on the Valley Pike with Hatch and his 250 men in the lead followed by Douty’s five companies, and Collin’s detachment of the 1st VT Cavalry. Lieutenant Colonel Douty was in the rear attending to Cilley. What would follow was known as the Action or Engagement at Middletown interpreted by the sign below in the center of Middletown.

As General Hatch approached the northern end of the town, he saw the trap Ashby had set in place and instead of riding straight into it he made an abrupt left hand turn onto Capon Springs Road (modern day Chapel Road) and escaped to the west followed by Company B and H of the 1st ME Cavalry. The rest of the 1st ME and 1st VT Cavalry with their vision obscured by the dust from Hatch’s men continued straight forward into the trap. Several of Chew’s shells hit the column causing several horses from the 1st ME Cavalry to fall creating a pile up in the road with many riders unhorsed. The 1st VT Cavalry behind them added to the pile up. The Louisianans fired into the pile and the approaching riders. Those that escaped the pile became caught up in the baggage wagons. Some of the men tried to escape on foot but were caught by Ashby’s Cavalry. In 30 minutes, the rout of the rear guard was complete. Two hundred Federals were captured along with their horses. At 4:00 PM Jackson sent a courier to Ewell to move on Winchester as soon as possible. Stonewall planned to continue north and fall upon the rear of the column when suddenly he heard artillery fire further south in Strasburg. This suggested to Jackson that he may have fallen upon the front or middle of Banks’ army. There would be no reason for artillery to be behind the rearguard. Jackson turned his force south and headed toward the sound of the guns. Little did he know that he was sending the majority of his army toward 5 cannons and their artillerists, 75 infantrymen and a few companies of cavalry. This was Banks’ rearguard. It was a huge mistake as Jackson would lose his chance to strike the true rear of Banks’ column and trap him between the two parts of his force before they could reach Winchester.

Seeing the artillery Jackson felt that he had split Banks’ army here, still not realizing he was facing a small rearguard. He ordered Ewell to not advance any further toward Winchester and to send General Elzey’s brigade to Middletown thinking that a sizable Union force was marching toward him. This would leave Ewell with little more than a brigade under his command. Given the 13 miles between Jackson and Ewell, allowing for the time to deliver the order and for Elzey to get to Middletown, which would take close to 6 hours, he would likely not arrive until 10:00 PM.

Captain Abert realizing that Cedar Creek could be easily forded decided to abandon the bridge there and head north with Captain Charles Collis’ 80 Zouaves. Near Middletown they ran into Taylor’s Louisiana Brigade. As Abert moved his men back to the south, just beyond Belle Grove mansion on a rise was the five-gun Union Battery F of the PA Light Artillery commanded by Captain R.B. Hampton. The Zouaves took up position behind the battery. Colonel Charles Tompkins and five companies of the 1st VT Cavalry joined the Zouaves on the ridge. As Taylor’s men advanced the Federals moved off the ridge to the heights south of Cedar Creek. Here they were joined by a few more infantry that had fallen back from Middletown. They retreated further south to Hupp’s Hill. At 5:30 PM a black civilian led them to the summit of Hupp’s Hill and the Capon Road that skirted the valley to the west to escape.

A small group of 40 cavalrymen and artillery under Ashby had broken off from the main Confederate column and pursued to the north. Their movements were detected by Union signal stations north of Middletown. General Alpheus Williams sent the 27th IN south to deal with them. Just south of Newtown Ashby’s Cavalry charged and pushed the Hoosiers back to Newtown. Colonel Gordon headed there with the 28th NY, 2nd MA and a section of Battery M of the 1st NY Light Artillery (about 1400 men) halting heir advance.

As the battle continued past 5:30 PM Jackson finally came to the conclusion that he was facing a small rearguard. Leaving one regiment at Cedar Creek he headed back toward Middletown sending a courier toward Ewell with an order to advance on Winchester. He then realigned his force putting the Stonewall Brigade at the head of the column. At 6:00 PM still with no word from Jackson Ewell had already decided to advance toward Winchester with his reduced force of less than 2,000 men. As Jackson moved north toward Newtown, he was disturbed to see members of Ashby’s Cavalry and Louisiana infantry pillaging Banks’ wagons. The Union rearguard at Newtown was holding their own against Confederate artillery. Union General Hatch’s men rejoined the column here after escaping from Middletown. At this point Colonel Gordon decided to withdraw his large rearguard to Winchester burning as many of the disabled wagons as he could along the way.

Fearing that Banks had been cutoff at Middletown, Lincoln ordered Frémont to move his Mountain Department immediately to Harrisonburg from Franklin. He also suspended the plan to add McDowell’s 38,000-man and 86-gun Department of the Rappahannock to McClellan’s Army of the Potomac.

As the sun was setting and 7:30 PM approaching, it was becoming clear that Banks’ army was going to make it to Winchester. Jackson had multiple opportunities to achieve his goal to cutoff Banks. He had failed to send scouts out in the early morning hours to reconnoiter the three roads between the Front Royal-Winchester Road and the Valley Pike to determine if Banks was moving toward Winchester. Ewell wasted most of the day waiting for orders from Jackson when he could have been moving up the Millwood-Newtown Road. Jackson also misjudged the size of the Union force facing him near Cedar Creek which was the final nail in the coffin when he was delayed by a force of under 100 men.

Next- On the Eve of Battle

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