Sweet Beginnings
Sweetest Day might not be as famous as Valentine's Day, but its story is just as tender. In 1921, in Cleveland, OH, a group of candy makers in the area started the holiday as a means of enhancing the lives of orphaned children, the elderly, and other marginalized individuals. They distributed candy and small gifts as a way of spreading cheer and compassion throughout the community. Over the years, what was once a humble act of kindness in a single location soon rippled across the Midwest. Sweetest Day is most popular in Michigan, Illinois, and Indiana, but its spirit of benevolence reaches far beyond those states.

Sweetest Day vs. Valentine’s Day
Sweetest Day means more than just romantic love, whereas Valentine's Day is associated mainly with romantic love. It's about being kind to everyone, not only your sweetheart, but also friends, family, and even strangers. Both holidays are about love, but Sweetest Day is primarily about kindness. It reminds us that everyone knows the language of giving.

Today’s Sweetest Day
Traditionally, Sweetest Day was marked with candy and flowers, but over time, gift-giving has expanded to include more extravagant gestures. Today, couples often celebrate with romantic surprises, while families exchange thoughtful tokens of appreciation. Jewelry is becoming one of the most significant ways to remember the day. It is a keepsake that lasts a lifetime, reminding the person who receives it of love and attention every time they wear it. 
Jewelry = the Perfect Sweetest Day Gift
A piece of jewelry is a beautiful way to make a statement and tell a story. For instance, a sparkling diamond ring can symbolize a new or enduring love, a heart-shaped pendant can represent devotion, and a personalized bracelet can serve as a daily reminder of shared memories. Sweetest Day is even becoming a popular occasion for proposals, so engagement rings are a logical choice.

Necklaces, earrings, or birthstone jewelry make great gifts for people who want something meaningful yet practical. These gifts are the perfect way to show your love on Sweetest Day: they last forever, unlike candy or flowers.

FAQs About Sweetest Day & Jewelry

- When is Sweetest Day celebrated?
The third Saturday in October each year. This year, it’s October 18, 2025.
- Is it only for couples?
No, it’s about kindness, appreciation, and love for anyone special in your life.
- Why Jewelry Instead of Flowers or Candy?
Jewelry lasts forever and carries sentimental value that won’t wilt or stale like flowers or chocolate will.
- Is Sweetest Day a Good Time to Propose?
Absolutely! Sweetest Day is becoming a perfect occasion for romantic milestones.

Sweetest Day may have started with sweet treats and small gifts, but its message of kindness is timeless. Today, it’s an opportunity to express love in a lasting way—with jewelry that tells your unique story.

Whether it’s a dazzling engagement ring, a heart-shaped pendant, or a personalized bracelet, Rogers & Hollands | Ashcroft & Oak help make Sweetest Day unforgettable.

Visit your nearest store or browse online to find the piece to express your love and gratitude.

Need help choosing? Book an appointment with a live Jewelry Expert. You can even design your own. Our custom design specialists will bring your vision to life in real time.