Well, it was started by a candy company employee, who believed in giving to those we were forgotten and less fortunate. According to a article I read on theromantic.com, Sweetest Day observation originated in Cleveland, Ohio in 1922. Herbert Birch Kingston, a philanthropist and candy company employee wanted to bring happiness into the lives of orphans, shut-ins and others who were forgotten. With the help of friends, he began to distribute candy and small gifts to the underprivileged.
This holiday is primarily a regional observance celebrated in the Great Lakes region and the Northeast, Sweetest Day is gradually spreading to other areas of the country. People tend to take the Sweetest Day tradition with them when they move. Ohio is the top state for Sweetest Day sales, followed by Michigan and Illinois. Texas, California and Florida are among the top 10 states in sales. Over the years, Sweetest Day has evolved into a time to express romantic love and also to show appreciation to friends.
Sweetest Day is observed the 3rd Saturday in the month of October.
Read the complete article at http://theromantic.com/sweetestday.htm