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Sweetest Day is a holiday primarily celebrated in the Midwestern U.S. states of Illinois, Michigan and Ohio, but recently seems to have gained popularity in other regions, particularly the Northeast. It is celebrated on the third Saturday in the month of October.

The holiday is said to have begun in the city of Cleveland, Ohio in 1922. Candy store employee Herbert Birch Kingston put together a group of citizens to provide small gifts to homeless people, orphans, and others who had fallen on hard times. This tradition now seems to largely involve giving small presents, such as cards, candy and flowers, to family, friends, and lovers.

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