Sweetest Day is celebrated on the 3rd Saturday in October. This year Sweetest Day falls on October 19th. This is Sweetest Day - A day inspired by the love and friendships of those we cherish. Sweetest Day’s history actually lies in October of 1922, led by a kind-hearted confectioner named Herbert Birch Kingston who passed out over 20,000 boxes of candy to forgotten populations in the Cleveland, Ohio area… the poor, orphans and shut-ins. Remember to brighten someone's day this October!