Valentines's Day is celebrated in February! Every February 14th we support Hallmark & Hershey's & florists nationwide. There's a day that's very similar to the annual winter day for romancing...it's Sweetest Day. It's recognized the third Saturday in October. Therefore, every year it's a different date. This holiday is quite young. In 1921, a man named Herbert Birch Kingston distributed candy to the orphans and homeless around Cleveland, Ohio.