The holiday was founded in Cleveland in 1922 by Herbert Birch Kingston, a philanthropist and candy company employee.  The holiday was created with the intention to bring happiness into the lives of orphans, shut-ins, and others who were forgotten by distributing candy and small gifts.

Sweetest Day is primarily celebrated in the Great Lakes region and the Northeast; however, it is gradually spreading to other areas of the country. Today, the holiday is the most popular in Ohio, followed by Michigan and Illinois. Texas, California, and Florida are also seeing a significant increase in those celebrating Sweetest Day.