During the Sioux Indian War of 1862, fighting centered on New Ulm after the Sioux Indians at the Red Wood and Yellow Medicine Agencies on the upper waters of the Minnesota River rose in open rebellion on August 18, 1862, massacring nearly all the whites in and about the agencies. Under Chief Little Crow, they moved downriver toward New Ulm and on August 19 entered Milford, about seven miles west of New Ulm, where many inhabitants were killed. That afternoon about one hundred warriors attacked New Ulm, killing several citizens and burning buildings, but they failed to carry the hastily built barricades. As the battle continued, the advance of Captain Charles E. Flandrau's company from Nicollet County, about fifteen strong under L.M. Boardman, entered the town and the attackers withdrew, while Captain Jacob Nix had directed the defense up to that time. At 9 p.m. on August 19, a larger force including Flandrau's company and a company from Le Sueur County arrived and took possession of the town, and several hundred more reinforcements came later. On August 20, Captain Flandrau was chosen Commander in Chief and the defenses were strengthened. On August 23, six hundred and fifty Indians again attacked New Ulm at half past nine in the morning and besieged it until noon on August 24. The assault was vigorously executed and desperately resisted, and one hundred and eighty buildings were destroyed, leaving only the part of town within the barricades. Thirty-four defenders were killed and about sixty wounded, and reinforcements under Captain Cox of St. Peter arrived at noon on August 24. On August 25, the town was evacuated and the inhabitants were safely conveyed to Mankato. The fighting was remembered as aided by citizens from Blue Earth, Nicollet, Le Sueur, and adjacent counties who came to rescue the people of Brown County and helped confine the depredations to the border rather than the heart of the state.