On May 9, 1862, the five 1st Maine Cavalry companies assigned to the “Railroad Brigade” of Col. Dixon Miles received orders from him to “March forthwith via Winchester to New Market” in the Shenandoah Valley and “wait for nobody, but be in haste.”
The War Department had assigned Maj. Gen. Nathanial Banks and his 5th Corps to bottle up Gen. Thomas J. “Stonewall” Jackson and his men in the Valley so they could not reinforce Confederate troops defending Richmond. Banks needed more cavalry, hence the May 9 orders hurrying the 1st Maine to Winchester.
Banks moved his troops “up” the Valley, and the five Maine cavalry companies pulled picket duty and scouted as directed. The recently promoted Lt. Col. Calvin Douty of Dover led companies B, H, and M to Woodstock on Tuesday, May 20; the cavalrymen skirmished with enemy troops there and at Strasburg.
On Friday, May 23, Jackson’s troops all but annihilated an isolated Union garrison at Front Royal. From there Jackson intended to march north and capture Winchester, thus trapping all Union troops remaining in the Valley as far away as Strasburg.
Banks learned about Jackson’s Front Royal attack on Friday evening. Knowing that he was heavily outnumbered, he ordered his men to march for Winchester, with the army’s wagon train lumbering along the Valley Pike (modern Route 11). Banks also ordered Brig. Gen. John Porter Hatch and his cavalry to guard the army’s rear.
Saddling up early on Saturday, May 24, the 1st Maine troopers halted before 7 a.m. at Middletown, a quiet town on the Valley Pike (modern Route 11). From Middletown a dirt road ran 7½ miles east to Cedarville on the Front Royal Pike. Hatch ordered Douty to take his five Maine companies and two 1st Vermont Cavalry companies and scout along the dirt road to see where Jackson and his army might be.
Cedarville, Middletown, and Winchester formed a rough right triangle, with the Front Royal Pike from Cedarville to Winchester being the hypotenuse and Middletown being the right angle. Jackson was hurrying his army to Winchester to trap the retreating Union army and destroy it.
Douty ordered company commanders to send sick soldiers and unhealthy horses on to Winchester. Inspecting his Co. B troopers and their mounts, Capt. Jonathan Prince Cilley saw Pvt. Charles A. McIntyre swaying on his feet beside his horse.
A pale countenance and swollen face indicated that the young cavalryman, “a boy I had enlisted in Warren in front of the schoolhouse where he was a pupil,” was obviously sick, Cilley realized.
“What is the matter?” he asked.
“Mumps,” McIntyre replied.
Cilley ordered him to “fall out” and join the other sick troopers.
“You enlisted me for active cavalry service, and now with the first chance of a fight you order me to the rear,” McIntyre responded, refusing his captain’s directive. He rode with Cilley toward Front Royal.
Riding through a rain-dampened landscape, Douty led the five 1st Maine Cavalry companies and two 1st Vermont Cavalry companies — A and C, commanded by Maj. Williams Collins — toward Cedarville. The crop road passed through fields and scattered woods; the Union troopers ran into Confederate soldiers about 1½ miles from the Front Royal Pike.
An initial exchange of gunfire tumbled the Confederates back for about a mile and likely saved Banks and his army — or at least most of it.
The Union cavalrymen then encountered “an old woman,” possibly a Unionist. She urged Douty to retreat; while Confederate Gen. Richard Ewell advanced on Winchester, Jackson had turned west on the dirt road to cut off Banks at Middletown.
If Ewell and Jackson sprang their trap, Banks the cat would never get out of the bag; neither would Douty and his 400 men.
Likely thanking the woman for her information, Douty told her not to worry because 40,000 Union soldiers approached from the west. The informer scuttled away; Douty deployed his men “in [a] line of battle in front of a large belt of timber which extended on both sides of the road,” said Edward Parsons Tobie, a young Maine trooper who later wrote the official history of the 1st Maine Cavalry.
Skirmishers probed east, discovered advancing Confederate cavalry commanded by Turner Ashby, and fired; two Confederates fell. Additional shooting broke out, and Jackson realized that he might be facing a Union attack.
Fulfilling a double agent’s role, the woman who had recently spoken with Douty now told Jackson about the “forty thousand Yankees” approaching his left flank. While they could see Douty’s riders spread along the tree line, Ashby and Jackson could not see what the woods might conceal.
Confederate gunners unlimbered their cannons and fired on the distant Union soldiers and into the trees to flush out hidden troops. Ashby’s artillery drew no counter-battery fire, sent no infantrymen scurrying for cover; only cavalry opposed some of Jackson’s finest troops, and cavalry could not hold long against artillery and infantry.
But the resolute Douty, an almost middle-aged man who could have cited his grizzled years as sufficient reason to avoid military service, bought time for the Union troops scurrying north on the Valley Pike behind him. He gradually pulled back his men; for the next four hours and despite being outnumbered about 10-to-1, he utilized “every advantageous spot of ground in checking the advance of the entire rebel force on the dirt road to Middletown,” Tobie recalled.
Armed only with “pistols and sabres,” the Union troopers withdrew through the scattered woods and across adjoining fields, Cilley said. One Maine cavalry captain led his company in a successful charge against Confederate troops; Cilley questioned the charge’s necessity, but with no Union men lost, the action was moot.
Douty’s appearance upset Confederate plans. “Jackson halted his army on the Front Royal pike, and sent all his cavalry, one battery, and a portion of his infantry (300 Louisianans)… to repel Douty’s attack and ascertain his strength,” Cilley said. Jackson also ordered Ewell, then not far from Winchester, to halt while the Union threat from Middletown was assessed
The sun gradually appeared and dried the muddy roads as, a few miles to the west, the cumbersome Union wagon train and its escorting infantry moved “in a straggling manner on the Strasburg pike” toward Winchester, Cilley learned after Douty’s battalion trotted into Middletown about 2:30 p.m.
A former Piscataquis County sheriff had outwitted Stonewall Jackson for several hours, but Jackson had the final “say.”
He was right behind the Union cavalrymen.
Next week: Horsemen in the Shenandoah: Part III — The “Middletown Disaster”
Brian Swartz can be reached at email@example.com. He would love to hear from Civil War buffs interested in Maine’s involvement in the war.