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Robert Huston Milroy was born 11 June 1816 near Salem, Indiana. His father, General Samuel Milroy, moved the family to Carroll County, Indiana, in 1826. In 1843, the younger Milroy graduated from Norwich University, a Vermont military institution, with Masters Degrees in Arts, Civil Engineering, and Military Science. He traveled throughout New England, teaching fencing and boxing, for several months. Upon his return to Indiana, he commenced legal studies, but interrupted them twice for military pursuits, first in Texas and then in the Mexican War, serving as Captain in the First Indiana Infantry. He graduated from the Indiana School of Law at Bloomington and was admitted to the bar in 1850. The governor of Indiana appointed Milroy President Judge of the Eighth Judicial District in 1852. Two years later, he moved to Rensselaer, Indiana, where he established a practice of law lasting until the outbreak of the Civil War. Milroy served with distinction and some controversy in the Civil War, rising in the ranks to Major General by 1862, but was also tried and acquitted of cowardice.

Following the war, Robert Milroy resigned his commission and partnered with Judge Gould to form a law firm in Delphi, Indiana. He declined an appointment as U. S. Marshall of Wyoming Territory in 1871, but in 1872, moved to Olympia, Washington, to serve as Superintendent of Indian Affairs, Washington Territory. When that position was abolished, Milroy became U. S. Prosecuting Attorney, then in 1875, U. S. Indian Agent for Puyallup, Nisqually, and other tribes in southwest Washington. Finally, Milroy became an agent for the Yakima (Yakama) Indians in eastern Washington from 1882-1885, replacing James Wilbur. He was removed in 1885 due to a change in political control of the Executive Branch.

In 1849, Robert Milroy married Mary J. Armitage, daughter of Valerius Armitage, a major contractor in the construction of the Wabash and Erie Canal. They had seven children. Sons Bruce and Walter practiced together as attorneys in the North Yakima, Washington Territory, firm of Milroy, Irwin and Milroy.

A lifelong Presbyterian, Milroy served as an Elder in the church, and was a strong supporter of the temperance movement. Milroy was also a member of the Indiana Second Constitutional Convention of 1850. His involvement in transportation projects included his election by the General Assembly of Indiana as Trustee of the Wabash and Erie Canal in 1867, and the instigation of two railroads: from Indianapolis to Chicago, passing through Delphi, Indiana; and Olympia to Tenino, Washington. Milroy died in Olympia, Washington, in March 1890, and is buried in the Masonic Cemetery.