Sweetest Day is in 2019 on a Saturday (October 19, 2019)

This is no holiday and therfore no day off. You always can take the day off by yourself to celebrate Sweetest Day.

When is Sweetest Day?
Date	Week Number.	Days until Sweetest Day
Saturday 19 October 2019	Week 42	184
Saturday 17 October 2020	Week 42	548
Saturday 16 October 2021	Week 41	912
Saturday 15 October 2022	Week 41	1276

The first Sweetest Day was pronounced as October 8, 1921 in Cleveland. The Cleveland Plain Dealer`s October 8, 1922 edition, which chronicles the first Sweetest Day in Cleveland, states that the first Sweetest Day was planned by a committee of 12 confectioners chaired by candymaker C. C. Hartzell. The Sweetest Day in the Year Committee distributed over 20,000 boxes of candy to "newsboys, orphans, old folks, and the poor" in Cleveland, Ohio See also Sweetest Day on Wikipedia.

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