Malley's chocolate covered grapes.It’s no surprise that Sweetest Day was always a big deal for Mike Malley when he was growing up. After all, he is one of Bill and Adele Malley’s six children who grew up watching their parents build the Malley’s Chocolates empire in Brookpark.

“Sweetest Day was something my family actively participated in,” he recalls. “One year, my dad had us and some neighborhood friends pile into his station wagon, and we went to help pack candies at another local shop.”

In fact, Sweetest Day has always been about altruism, building community, and showing kindness—and sharing candy. First celebrated in Cleveland, the local confectioners came together for one day to do good for the community.

Since its first iteration in 1916, the holiday has been about improving the lives of others. Although it is often believed that Sweetest Day was invented by candy and greeting card companies to boost business, Malley’s president and CEO Megan Gillum says the origins are far more altruistic.

“Sweetest Day was born right here in Cleveland, and there’s something really special about being part of a tradition that has brought people together for more than a century,” she says.

The holiday officially launched in Cleveland in 1922 by advertising executive Herbert Birch Kingston, who wanted to spread kindness to those who were often forgotten. He distributed bags of candy to orphans and others in need, and that simple act of kindness grew into a tradition—especially around the Great Lakes region, in cities like Buffalo and Detroit.

Today, Sweetest Day may hold more of a “lovers’ holiday” image in the minds of many, but Malley’s still sees the sweet October holiday as a way to spread the love.

Sweetest Day History.This week, staff at Malley’s Chocolates’ 18 locations are preparing for Sweetest Day on Saturday, Oct. 17, when customers can share a little sweetness with two seasonal favorites: chocolate-covered strawberries and chocolate-covered grapes.

The limited-edition treats are a longtime Malley’s tradition for the October holiday, offering a delicious way to celebrate the day’s spirit of kindness and connection.

Chocolate-covered strawberries and grapes have been Malley’s Sweetest Day and Valentine’s Day traditions for decades, Gillum says. The strawberries made their debut in 1986, followed by the chocolate-covered grapes in 2005, which quickly became a customer favorite. For the seasonal treats, Malley’s selects its sweetest fruits to pair with milk chocolate.

“As Malley’s looks to the future, we want to continue building on that legacy by creating new memories, celebrating old traditions, and reminding people that even the smallest gesture of kindness can make someone's day,” says Gillum.

The strawberries and the grapes will arrive at all 18 Malley’s stores this Friday, Oct. 16 at 12 p.m., and will be sold while supplies last. Each variety is priced at $32.95 a package. Customers can call their favorite location for pre-orders.