People observe Flag Day on June 14 because it was on this particular day in 1777 that the adopting of the American flag by the Second Continental Congress transpired. In 1916 President Woodrow Wilson gave a proclamation, which set up June 14 as the date that Americans would honor our flag. The Congress then eventually established it 33 years afterward in 1949.
This particular specific day in which we honor our flag is neither a federal nor a state holiday except one state, that being Pennsylvania. They started commemorating Flag Day as a state holiday on June 14, 1937. There is a parade in Troy, New York that honors the flag and is the largest Flag Day parade in the nation with an average attendance of 50,000 people. George Morris of Hartford, Connecticut is considered to have been the first to suggest the observance of a "Flag Day" and although the tradition did not continue, it was celebrated for the first time in Hartford in 1861.
In 1885 Cigrand J. Bernard, a schoolteacher in Waubeka, Wisconsin, was the earliest to formally honor Flag Day in Waubeka at Stony Hill School. From that time on, Cigrand encouraged patriotism, and respect for the flag, and the need to observe a very special day in its honor all around the country. In June 1886 when attending dentistry school in Chicago, the Chicago Argus newspaper released his initial public proposal for the yearly observance of the birth of the United States Flag in a short article titled "The Fourteenth of June". Then in 1888, became the editor-in-chief of American Standard, a magazine established by a Chicago group known as "Sons of America", encouraging reverence for American symbols by authoring articles. His write-ups were not only shared in American Standard, but in numerous other magazines and newspapers as well. And in 1894, over 300,000 school children in Chicago commemorated Flag Day. Cigrand continued to become the president of the American Flag Day Association and the National Flag Day Society, with the help of these particular organizations; Cigrand was able to deliver over 2,000 speeches about patriotism and the American flag. He later resided in Batavia, Illinois from 1913 up until his death on May 16, 1932. Several regard him as the "Father of Flag Day".
William Kerr of Collier Township, Pennsylvania, who established the American Flag Day Association of Western Pennsylvania in 1888 and serving as its own national chairman for fifty years, attended the signing of the Act of Congress in 1949 by Harry Truman, which in turn formally established the observance of this day. George Boch, a kindergarten principal in New York City, celebrated this day in his school in 1889. Elizabeth Duane Gillespie, the president of the Colonial Dames of Pennsylvania, in 1893 tried a resolution for the establishment of a June 14th Flag Day. All these are but a few notable patriots who championed the national observance of Flag Day.