The origins of Sweetest Day

Hesser Ann Pennington2
On the very first Sweetest Day, actress Ann Pennington presented 2,200 Cleveland newspaper boys with boxes of candy to express gratitude for their service to the public.

By Mitch Allen

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One of the most confusing concepts in all of Northeast Ohio culture is this thing called “Sweetest Day.” 

Most people living outside of Northeast Ohio have never heard of it, and most people living in Northeast Ohio can't tell you how it got started (no, it was not invented by American Greetings). And although everyone in Cleveland seems to acknowledge the day, it’s difficult to find a guy in a Browns jersey who will admit to celebrating it.

The problem with Sweetest Day is that it has a massive inferiority complex, largely because we have come to refer to it as “a second Valentine’s Day.” 

Well, being a second Valentine’s Day is like being the team that went to the Super Bowl and lost. Or worse, that guy who orbited the moon while Neil Armstrong and Buzz Aldrin bounced around on its surface. (His name, by the way, is Michael Collins).

In fact, Sweetest Day (the third Saturday in October) is not a second Valentine’s Day. It has its own unique and rightful origins.

Sweetest Day began in Cleveland in 1922 when a man named Herbert Birch Kingston decided to bring a little happiness into the lives of orphans, shut-ins and others who were often forgotten. With the help of friends, he distributed candy and small gifts to Cleveland’s underprivileged. 

On the very first Sweetest Day, actress Ann Pennington, who starred in many films including 1925’s The Mad Dancer (in which she shocked the nation by appearing nude), presented 2,200 Cleveland newspaper boys with boxes of candy to express gratitude for their service to the public. 

Another popular actress, Theda Bara, who starred in over 40 films from 1915 to 1926, gave away 10,000 boxes of candy to patients in Cleveland hospitals and to those who came to watch her film in a local Cleveland theater.

So although Sweetest Day has its roots in random acts of kindness, we have somehow reduced its status to a second-rate Valentine’s Day. And that’s too bad, especially considering how fast it’s spreading.

According to greeting card company American Greetings, people from Northeast Ohio are taking the holiday with them when they move, introducing it to communities all over the country. 

Ohio is still the top state for Sweetest Day sales, followed by Michigan and Illinois. Even Texas, California and Florida are among the top ten. The holiday’s popularity is growing so fast that American Greetings and Hallmark now produce hundreds of different greeting card designs for Sweetest Day, compared to only a handful of versions in 2000.

We should be proud that Sweetest Day is a Northeast Ohio phenomenon with solid, national momentum. This year, on the third Saturday in October, I can’t think of a better way to share our culture with the rest of America than with a little love and tenderness.

Who knows, soon those traits may grow in popularity, too.