The American Association of the Friends of Kosciuszko at West Point was created and incorporated in Massachusetts in 2003 by Anthony J. Bajdek, an Associate Dean and Senior Lecturer in History at Northeastern University in Boston. In 2006, the United States Internal Revenue Service designated it to be a 501(c)3 tax-exempt charitable entity. Assisting him in his role as Founder / President, was an initial Executive Board made up of five Vice Presidents: Alicja Altenberger of Massachusetts, Frances X. Gates of New York, Genia Golda of New York, George Katucki of New York, and Stephen N. Olejasz of Virginia, along with Scretary / Treasurer, Cynthia J. Bajdek of Massachusetts. Of that original Executive Board, only President Bajdek, Executive Vice President Stephen N.Olejasz and Secretary / Treasurer Cynthia J. Bajdek remain.

The Kosciuszko Conference is held annually on a full-day basis in the Thayer Hotel on the grounds of the United States Military Academy in West Point, New York. Its structure is purely academic in nature, bringing together university-level academicians, authors, historians, members of Poland's and Lithuania's military, members of Poland's and Lithuania's defense ministries, West Point faculty, and think-tank specialists from Washington, DC, all of whom seek to illuminate the life and times of Kosciuszko in the United States as well as in Poland, and/or to illuminate contemporary security issues confronting NATO, the European Union, and the United States viv-a-vis the Russian Federation. In 2019, the Association held its 16th Annual Kosciuszko Conference at West Point.

The Observance is held annually in the spring at the site of the Kosciuszko Monument, which is the world's second oldest monument to Kosciuszko; the world's oldest monument to him is the Kosciuszko Mound (Kopiec Kosciuszki) in Krakow, Poland. The Kosciuszko Monument of West Point was paid for through voluntary fund-raising action among members of the United States Military Academy's Corps of Cadets and was dedicated on July 4, 1828. The original base and column, being the award-winning design submitted on March 10, 1825 by one-time USMA Cadet and later Maryland attorney and philanthropist, John H. B. Latrobe (1803-1891), became in effect the Academy's first major commemorative monument during the Superintendence (1817-1833) of Sylvanus Thayer (1785-1872), a native of Braintree, Massachusetts, who encouraged the Corps of Cadets to select a West Point hero of the American War of Independence for whom a monument was to be built. The Corps of Cadets selected Tadeusz Kosciuszko and Latrobe's design. Eighty-five years later, upon the initiative of the Polish American clergy and laity who raised the necessary funds, the heroic-sized bronze statue of Kosciuszko, being the work of D. Borgia, a sculptor employed by the New York firm, Frederick Pustel and Company, was mounted atop Latrobe's original column and base of 1828 and unveiled with appropriate ceremonies on September 1, 1913. Borgia's work is similar to the statue of Kosciuszko conceived and cast by Polish sculptor, Antoni Popiel (1865-1910), that has graced Lafayette Square in Washington, DC since 1910.

After the first Observance on July 4, 1828 the frequency of subsequent 19th century and early 20th century Kosciuszko Observances is yet to be fully documented, except for the one on September 1, 1913. It is generally accepted in the oral history of the local Polish American communities in downstate New York, especially those of Rockland County, that the Kosciuszko Monument observances occurred somewhat regularly through the mid-20th century except for the interruption caused by World Wars I and II. Subsequent to WW II, the observances occurred with greater regularity, so much so that today the United States Military Academy never cancels for reasons of inclement weather what has become the Annual National Tadeusz Kosciuszko Observance. The American Association of the Friends of Kosciuszko at West Point also invites speakers for the Annual Kosciuszko Monument Observance. In 2017, which had been designated by UNESCO as the "Year of Kosciuszko" worldwide, both Poland's Ambassador to the United nations, Boguslaw Winid, and Lithuania's Ambassador to the United Nations, Raimunda Murmokaite, accepted the invitation and spoke at the Kosciuszko Monument ceremony.

While submitting his competitive design for the consideration of the Corps of Cadets, Latrobe included in his accompanying letter of March 10, 1825 a lyrical, deeply prophetic sentence about an appropriate identifying inscription for the Monument:

"Let KOSCIUSZKO simply be the inscription and on the lowest steps in smaller characters, 'Erected by the Corps of Cadets of the USMA,' and while your River flows and your country exists, no one will be at a loss to understand the Monument, its purpose, and its location."

The American Association of the Friends of Kosciuszko at West Point, Inc. is dedicated to ensuring that in the United States at least, "no one will be at a loss to understand the Monument, its purpose, and its location," ever.