In June 1882, he graduated number thirty-three in a class of thirty-seven from the United States Military Academy (USMA) at West Point, New York.

Among his classmates there at the academy were several men who would, like Allaire himself, eventually attain the rank of brigadier general or higher during their military careers, such as Edward Burr, Lansing H. Beach, Adelbert Cronkhite, John T. Thompson, Charles Treat, Edward A. Millar, Richard W. Young, Benjamin Alvord Jr., George W. McIver, Henry T. Allen, William H. Sage, and Thomas B. Dugan.

After arriving back in the United States, he served at Fort McPherson in Georgia and Plattsburg Barracks until April 1903 when he returned to his regiment in the Philippines, where he stayed until December 1904.

After coming back to the United States a second time, Allaire performed recruiting duty until 1908 when he became military attaché at the American Embassy in Vienna.

[1] Upon his return in 1911, he served in the office of the Chief of Staff in Washington for a short time before joining the Fourth Infantry at Fort Crook in Nebraska.