Sweetest Day

Sweetest Day is observed on the third Saturday in October each year, and in 2025 it will fall on October 18. Originally rooted in simple acts of kindness and generosity, this heartwarming occasion has grown into a celebration of love, friendship, and thoughtfulness. It’s a day to share sweets, thoughtful notes, or small gestures not just with romantic partners, but with anyone who could use a reminder that they’re appreciated and not forgotten. Though it may be lesser known nationally, in many parts of the Midwest, Sweetest Day holds a special place in people’s hearts.

History of Sweetest Day

Sweetest Day has its earliest roots in 1916, when the National Confectioners’ Association promoted a “Candy Day” in October as a way to encourage people to buy and share sweets. That early effort faded, but a few years later, in 1921, a Cleveland-based candy company employee named Herbert Birch Kingston revived the concept with a deeper purpose. He organized the distribution of candy and small gifts to orphans, the elderly, hospital patients, and underprivileged children—people who were often overlooked and forgotten.

From this single act of kindness, the idea spread. Local businesses and volunteers joined in, and Sweetest Day quickly became an annual regional tradition. Eventually, the holiday settled into the third Saturday of October and was embraced not only in Ohio, but also in parts of Michigan, Illinois, and other neighboring states. Though commercialized over time, its foundation remains rooted in kindness and remembrance.

Why Sweetest Day matters

There’s something genuinely special about a day that blends sweetness with sincerity. Sweetest Day isn’t just about candy and cards—though those are part of the charm—it’s about thinking of others and reaching out in thoughtful, personal ways. It might be a gentle reminder to thank someone who’s been quietly helpful, or to check in on a friend who’s going through something tough. It’s a little nudge toward empathy.

What makes Sweetest Day stand out is that it’s not just about romantic love. It includes friends, coworkers, neighbors, even strangers. It’s about bringing joy to someone else’s day in whatever way feels right—be it a small gift, a warm message, or just showing up. That spirit of simple, human connection is what gives this day lasting meaning.

Here are a few reasons the day endures:

• It promotes the idea that kindness is a gift everyone can give
• It encourages giving beyond romantic relationships
• It keeps alive a tradition rooted in community and empathy
• It reminds us that small gestures can have outsized emotional impact
• It helps local businesses (especially confectioners and card makers) in seasonal expression

How to Celebrate Sweetest Day

There’s no single right way to celebrate Sweetest Day—its beauty lies in its flexibility. You might surprise a friend or loved one with a favorite treat, or leave an anonymous note of encouragement for someone at work. For families, it can be a fun chance to bake something together or share sweets with neighbors. And for couples, it’s a lovely excuse for a simple date or thoughtful gift.

If you want to embrace the holiday’s original charitable spirit, consider donating small treats or essentials to a shelter, senior center, or hospital. Even volunteering a bit of time or checking in on someone who might be feeling lonely can carry the essence of what this day is all about. However you choose to celebrate, the goal is the same: make someone else’s day just a little brighter.

Some ideas:

• Give candy, sweets, or chocolates to someone special
• Send a heartfelt card or note to a friend or family member
• Do a small act of kindness for someone less expected
• Volunteer or donate sweets or small gifts to a community cause
• Use social media to share a message of care or appreciation

Sweetest Day Dates Table