What is Sweetest Day? Fall in love with this little-known holiday.

What is Sweetest Day
Illustrator: Jennifer van de Sandt

Did you know that, depending on where you live, October’s “sweetest” day might not be Halloween? Since the early 1920s, Sweetest Day has been celebrated on the third Saturday in October, though this charming holiday is comparatively obscure outside of the Great Lakes region. Here’s a look at how the holiday got its start, where (and why) it’s celebrated, and how you can take part, no matter where you live. 

What is Sweetest Day, anyway? It all started with Kingston’s sweet idea.

Sweetest Day was originated in Cleveland, Ohio, by a man named Herbert Birch Kingston. Kingston was a part of a committee of Cleveland-based candy manufacturers who were interested in reviving a failed holiday called “Candy Day.” This holiday had been proposed by a national confectioners’ group in 1916, but sugar rationing during World War I doomed the holiday before it got off the ground.

Kingston believed that traditional candy-giving occasions tended to leave many people out. He proposed to the committee that the “Candy Day” holiday be repurposed as “The Sweetest Day of the Year,” a more inclusive day that could help the less fortunate. On October 8, 1921, the candy makers on this committee distributed about 20,000 boxes of candy to Cleveland’s poor, elderly, unhoused, and orphans. This is considered to be the first official celebration of Sweetest Day.

In tandem with the holiday, the confectioners advertised the celebration in the Cleveland Plain Dealer with a special four-page “explainer” and recruited some of the era’s top movie stars to come to Cleveland and pass out candy. Popular actress Ann Pennington personally gave away candy to more than 2,000 Cleveland paperboys, and Theda Bara gave away 10,000 boxes to hospital patients and movie-goers at one of her films.

Candy makers in nearby Detroit, Michigan also celebrated Sweetest Day in 1921. Frederick Saunders, the founder of Detroit-based Saunders Candy Company, spread his enthusiasm for the new holiday to four of Michigan’s largest confectioner’s trade groups. These groups got together with the Red Cross to hand out thousands of bags of free candy to orphanages, hospitals, and shelters. They even dropped coupons for free candy from the sky, using 100 Army targeting balloons! 

Spreading the love

Increased mobility in the mid-20th century meant that transplanted Ohioans began to bring the holiday with them when they relocated to new areas of the country. Sweetest Day rapidly became popular throughout areas bordering Ohio, and national greeting card companies began making a few lines of cards for the occasion. As the holiday spread beyond the Cleveland area, it gradually transformed from a philanthropic holiday into a personal one, as people began to use the day to celebrate their own friends and family.

Sweetest Day continues to be most widely celebrated in the Great Lakes Region of the United States. According to Retail Confectioners International, Cleveland, Buffalo, and Detroit are the cities where Sweetest Day is most popular. In fact, some retailers in these cities report that, for them, Sweetest Day is a bigger day for candy sales than Mother’s Day! 

But Sweetest Day is also gaining popularity in the areas that border the Great Lakes States. Many people in places like Pennsylvania, New York, West Virginia, Kentucky, and the Dakotas observe Sweetest Day. Greeting card companies, including the national giants American Greetings and Hallmark, now make hundreds of different Sweetest Day cards.

How to celebrate Sweetest Day

Sweetest Day has a lot going for it. First of all, candy. True, there’s already a candy-laden holiday celebrated in October, but Halloween is primarily aimed at children, and there’s no particular emotional significance to the Halloween candy that kids get by knocking on doors. Sweetest Day gifts, by contrast, are given to specific people—including adults—as a gesture of affection.

And there are other choices besides candy, too. Flowers, kind acts, or other small gifts are also appropriate. Sweetest Day is meant to be a low-pressure way to remember someone with a pleasant surprise; it’s not an occasion that you have to sweat over how to get just right, like Christmas and Valentine’s Day.

Celebrating Sweetest Day is as simple as thinking about the people in your life that you love enough to surprise with a little treat or gesture, and then choosing something small you’d like to do for them. Friends, parents, siblings, special children in your life—everyone, not just a romantic partner, is a candidate for a little sign of your affection on Sweetest Day. 

If you’re a card giver, choose cards for the occasion and pen a special note inside each. If you love flowers, get a bouquet and distribute a flower to each of your loved ones. Acts of service are also very appropriate: rake your neighbor’s leaves, run errands for your mom, or do your partner’s chores for the day. And, of course, if you’re a sweets aficionado, celebrating is as simple as baking some cookies or buying a bag of candy and parceling out the goodies to friends and family throughout the day. 

You might even decide to celebrate like the O.G., Herbert Birch Kingston, and use a part of your day to sweeten the lives of the less fortunate. Drop off some small toys, coloring books, and crayons to a local children’s hospital; make a donation of socks and toiletries to a group that works with the unhoused; or grab some friends and volunteer at a food pantry, 

Unlike its better-known cousin, Valentine’s Day, Sweetest Day isn’t about singling out just one person for a grand display of love. Instead, it’s about many small acts of kindness. On Sweetest Day, celebrate by offering little reminders of your love to everyone you love. As the confectioners who first promoted Sweetest Day advised a year later, in the Sunday, October 8, 1922 edition of the Cleveland Plain Dealer, “steal enough time from the turmoil of routine affairs, to bring a bit of good cheer to those you love.” You’ll be amazed at how sweet it makes the day for you.

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