Sweetest Day Party Ideas & Guide: Celebrate Your Sweets

Between family, work and household chores, it’s all too easy to get caught up in your everyday shuffle. But when you do take the time to slow down, enjoy the moment and show others your gratitude for all they do, it pays off so much that you’re often left asking yourself, “why don’t I do this every day?”

That concept of showing your gratitude and paying it forward was the impetus for Sweetest Day. While it would be easy to write this off as another “Hallmark holiday,” invented to sell goods, Sweetest Day actually has no ties to Hallmark or any other greeting card company. The origin of the holiday tells a heartwarming story of a more innocent time that may even make the most cynical share some sweet treats with someone special on October 17.

Sweetest Day History

candy in bags

Sweetest Day is celebrated on the third Saturday in October and has been since the 1920s. While various sources list the first Sweetest Day as early as 1921 and as late as 1927, the story itself is quite consistent: Herbert Birch Kingston, an employee at a candy company, generously gave away candy to forgotten people who needed some cheer. He spent the day distributing candy to orphans, the disabled and the underprivileged.

Kingston’s idea caught on and soon others in Cleveland, Ohio, began participating in Sweetest Day. Soon, local movie stars Anne Pennington and Theda Bara joined in, sending thousands of boxes of candy to newspaper delivery boys, hospitals and movie theaters. Within a few years, the saccharine holiday was celebrated in surrounding cities and states, and to this day is still celebrated throughout the Midwest. Over the years, the focus has broadened to include sharing sweet treats with family, friends and other loved ones as well.

How to Observe Sweetest Day

woman holding cupcake

When it comes to celebrating Sweetest Day, the only real requirement is to share something sweet with someone. Whether it’s a box of chocolates for your assistant, your wife’s favorite macarons from the local French bakery or going to the local children’s hospital and distributing candy, the sentiment of thoughtfulness is all that matters. You don’t even necessarily need to give anything that tastes sweet; a sweet gesture like a from-the-heart greeting card or having fresh flowers delivered are also lovely ways to celebrate Sweetest Day.


Host a Sweetest Day Party

sweetest day party decorations

Send out invitations using candy-themed stationery to friends and family for an afternoon of festivities. Have all guests meet at your home bringing a variety of their favorite sweets to share. Once everyone has arrived, caravan down to the local shelter to volunteer serving a meal and share the treats with the less fortunate. After a few hours spent giving back to the community, return to your home with your nearest and dearest for a happy hour celebration. Serve simple hors d’oeuvres, libations and a delectable dessert bar, piled with cakes, cookies and candy. To present a Pinterest-worthy spread, be sure to use glass cake pedestals, tiered serving stands and footed apothecary jars in a variety of heights to create visual interest. Arrange the dessert bar on a long table along an uncluttered wall. Hang crepe paper garlands or honeycomb fans behind the dessert table in colors that complement the treats to ensure that none of the guests can miss your Sweetest spread.