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Updated: May 22, 2025
The battle on the Siboney-Santiago road, in the center of our line, began nearly two hours later than the battle at Caney. Grimes's battery, which had taken position on a hill near the Pozo farm-house, opened fire on the heights of San Juan about eight o'clock.
General Shafter went to the front to take personal command of the army on Wednesday, June 29. At that time the divisions of Generals Kent, Wheeler, and Lawton were encamped on the Siboney-Santiago road, between the high ridge of Sevilla, from which I had seen the city two days before, and a half-ruined house and plantation, two or three miles farther on, known as El Pozo.
Our only possible line of advance, in the center, was the Siboney-Santiago road, which ran, through a dense jungle, down the valley of the Aguadores River, crossed a small stream flowing into that river from the north, then crossed the San Juan River, another tributary of the Aguadores, and finally emerged from the forest directly in front of the San Juan heights.
Through this valley ran the Siboney-Santiago road, nearly parallel with a brook which had its source in the mountains to the northward, and after being joined by a number of other brooks coming from the same direction, fell into the sea through a notch in the coast rampart three or four miles east of Morro Castle.
The two columns encountered the enemy at about the same time. The Rough Riders, under Colonel Wood, began the attack on the mesa trail, and a few moments later General Young's command, on the Siboney-Santiago road, opened fire with three Hotchkiss mountain guns and began the ascent of the hill from the valley.
In every other direction except the one taken by this line of glades the camp was bounded by a dense tropical jungle through which the Siboney-Santiago road had been cut. The opening occupied by the hospital camp was covered with a dense growth of high wild grass, shaded here and there by small clumps of piñon-bushes, with a few larger trees of kinds to me unknown.
The plan was good enough, as far as it went; but General Shafter had made no reconnaissance on the Siboney-Santiago road beyond El Pozo, and was wholly ignorant not only of the strength of the enemy's position there, but of the nature of the country to be traversed.
The Siboney-Santiago road, at that time and for several days thereafter, was comparatively dry and in fairly good condition. It had to be widened a little in some places, and a company or two of soldiers from the Tenth Cavalry were working on it just beyond the Rough Riders' camp; but, as far as we went, loaded army wagons could get over it without the least difficulty.
At the same time the remainder of the corps, consisting of General Wheeler's cavalry division, the division of General Kent, and three batteries of light artillery, moved down the Siboney-Santiago road, and went into camp near the Pozo farm-house. At daybreak on Friday, July 1, both columns were in position, within striking distance of the enemy's intrenched line.
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