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Updated: June 2, 2025
Operations against the railroads had been allowed to slacken during Mosby's absence; now they were stepped up again. Track was repeatedly torn up along the Manassas Gap line, and there were attacks on camps and strong points, and continual harassing of wood-cutting parties obtaining fuel for the locomotives. The artillery was taken out, and trains were shelled.
In this way, General Julius Stahel, who had invaded Mosby's Confederacy with two brigades of cavalry and four pieces of artillery for the avowed purpose of utterly demolishing the Rangers, was so annoyed that he retired, thoroughly disgusted with an enemy "who only fought when they got their foe at a disadvantage."
Therefore, Wyndham would come looking for him at Middleburg. So, with a companion named Fountain Beattie, Mosby put up for what remained of the night at the home of a Mr. Lorman Chancellor, on the road from Aldie a few miles east of Middleburg. The rest of the company were ordered to stay outside Middleburg. Mosby's estimate of his opponent was uncannily accurate.
His first exploits had been so noised abroad that the young men from the neighboring counties and the soldiers at home on furloughs would request permission to join in his raids. He could easily muster fifty of these, known as "Mosby's Conglomerates," for any expedition. The opportunity for developing his ideas of border warfare was thus presented.
By this time, the rest of Mosby's force had mounted their horses, breaches had been torn in the fence at either side of the lane, and there were Confederates in both meadows, firing into the trapped men. Until the gate at the lower end gave way under the weight of horses crowded against it, there was a bloody slaughter.
When Beattie with six men rejoined Mosby, he found the latter sitting on a stump, munching an apple and watching the enemy through his field glasses. Wyndham, who had been searching Middleburg for "Mosby's headquarters," was just forming his men for a push on to Upperville, where he had been assured by the canny Middleburgers that Mosby had his camp.
However, Wyndham would be the ideal captive to grace a Mosby triumph, and a successful raid on Fairfax Courthouse, garrisoned as it was by between five and ten thousand Union troops, would not only secure Mosby's position in his own army but would start just the sort of a panic which would result in demands that the Union rear be re-enforced at the expense of the front.
I had not directed any special operations against these partisans while the campaign was active, but as Mosby's men had lately killed, within my lines, my chief quartermaster, Colonel Tolles, and Medical Inspector Ohlenchlager, I concluded to devote particular attention to these "irregulars" during the lull that now occurred; so on the 28th of November, I directed General Merritt to march to the Loudoun Valley and operate against Mosby, taking care to clear the country of forage and subsistence, so as to prevent the guerrillas from being harbored there in the future their destruction or capture being well-nigh impossible, on account of their intimate knowledge of the mountain region.
"'GENTLEMEN: It is a delicate question about this Indian trail, but, handled with proper deftness and dubiousness, I doubt not we shall succeed in some measure or otherwise, because the place where the route leaves the Lassen Meadows, over beyond where those two Shawnee chiefs, Dilapidated Vengeance and Biter-of-the-Clouds, were scalped last winter, this being the favorite direction to some, but others preferring something else in consequence of things, the Mormon trail leaving Mosby's at three in the morning, and passing through Jaw bone Flat to Blucher, and then down by Jug-Handle, the road passing to the right of it, and naturally leaving it on the right, too, and Dawson's on the left of the trail where it passes to the left of said Dawson's and onward thence to Tomahawk, thus making the route cheaper, easier of access to all who can get at it, and compassing all the desirable objects so considered by others, and, therefore, conferring the most good upon the greatest number, and, consequently, I am encouraged to hope we shall.
Mosby's party dismounted about 200 yards away from it and crept up on it, to find seven members of the Fifth New York squatting around a fire, smoking, drinking coffee and trying to keep warm. Their first intimation of the presence of any enemy nearer than the Rappahannock River came when Mosby and his men sprang to their feet, leveled revolvers and demanded their surrender.
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