The Following is from Wikipedia:
The first Sweetest Day was pronounced as October 8, 1921 in Cleveland. The Cleveland Plain Dealer’s October 8, 1922 edition, which chronicles the first Sweetest Day in Cleveland, states that the first Sweetest Day was planned by a committee of 12 confectioners chaired by candymaker C. C. Hartzell. The Sweetest Day in the Year Committee distributed over 20,000 boxes of candy to “newsboys, orphans, old folks, and the poor” in Cleveland, Ohio.[3] The Sweetest Day in the Year Committee was assisted in the distribution of candy by some of the biggest movie stars of the day including Theda Bara and Ann Pennington.[3]
There were also several attempts to start a “Sweetest Day” in New York City, including a declaration of a Candy Day throughout the United States by candy manufacturers on October 8, 1922.[4] In 1927, The New York Times reported that “the powers that determine the nomenclature of the weeks of October” decreed that the week beginning on October 10, 1927 would be known as Sweetest Week.[5] On September 25, 1937, The New York Times reported under Advertising News and Notes that The National Confectioners Association had launched a “movement throughout the candy industry” to rank Sweetest Day with the nationally accepted Mother’s Day, Father’s Day, and St. Valentine’s Day.[6] In 1940, another Sweetest Day was proclaimed on October 19. The promotional event was marked by the distribution of more than 10,000 boxes of candy by the Sweetest Day Committee.[7] The candy was distributed among 26 local charities. 225 children were given candy in the chapel at the Society for Prevention of Cruelty to Children on October 17, 1940.[7] 600 boxes of candy were also delivered to the presidents of the Jewish, Protestant and Catholic Big Sister groups of New York.
It appears that this Holiday is observed mostly in the Mid-West United States (especially Cleveland) on the 3rd Saturday of October… even though we aren’t in the Mid-West … it is an excuse to eat Candy!