Sweetest Day is celebrated each year on the third Saturday of October. Although often thought of by many as a second Valentine’s Day, Sweetest Day is actually a day meant to celebrate all the people who make your life special. It’s an occasion to make someone happy, a chance to celebrate and give gifts to relatives, friends, and associates.

Sweetest Day was founded around 1922 in Cleveland, Ohio by Herbert Birch Kingston who was a local candy company employee. Kingston sought to bring cheer and some happiness to the lives of those who were often forgotten. With the help of his friends, he began distributing candy and small gifts to children living in orphanages, those stricken with illness or disabilities, shut-ins, and others who were forgotten.

During the early years of the holiday, movie star Ann Pennington presented 2,200 Cleveland newspaper boys with boxes of candy to express gratitude for their service to the community. Theda Bara, another movie star of the period, also helped in establishing the holiday by giving away 10,000 boxes of candy to people in hospitals and to those individuals who came to watch one of her films at the Playhouse Square Theaters in Cleveland, Ohio.

Within a decade, the simple idea had gained such popularity that the city of Cleveland officially declared the third Saturday of October as Sweetest Day.

Over the years, the Sweetest Day idea of spreading cheer to the underprivileged has expanded to an occasion offering us the opportunity to remember not only the sick, aged, shut-ins, and orphans but also friends, relatives, and those individuals whose helpfulness and kindness we have enjoyed during the year.

The traditional observance of Sweetest Day involves the same types of gifts and acknowledgments as Valentine’s Day with the most popular being cards, flowers, chocolates, and candy.

Ann Pennington Sweetest Day is primarily a regional holiday celebrated in the Great Lakes region and the northeast. The observance of the holiday is gradually spreading throughout the United States as people relocate to various parts of the country and bring the regional celebration with them to their new homes. States that have the greatest observance of the holiday include Ohio, Illinois, Michigan, Indiana, and Wisconsin. Cities with the greatest observance of the holiday are Cleveland, Chicago, Detroit, and Buffalo. Sweetest Day is an original American holiday that is not based on any single group’s religious sentiment or on a family relationship. It is simply a reminder that a thoughtful word, deed, or small gift enriches the life of the recipient as well as the person giving it.