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What is Sweetest Day?

How to celebrate this Cleveland holiday creation where it all started.

Lexi Robinson October 09, 2025

Sweetest Day. You’ve heard of it. You're not quite sure what it is, and you’re probably feeling a little sketchy about buying into what many would describe as a "greeting card holiday." Hear us out, though. Celebrated the third Saturday in October, not only did this special day get its start right here in Cleveland, but we could all use a little more love in our lives, right?

Here's a rundown on how to get sweet with the people you love in The Land.

Legend Has It

Legend has it that back in 1921, a group of Cleveland-area candy makers got together to share ways they could bring happiness to the city’s less fortunate. So, they distributed candy and chocolates to the sick, elderly and orphaned on what they lauded as “Sweetest Day.” The day became popular year-after-year and later took off when companies — like Cleveland-based American Greetings — spread the concept nationally. Here are some ways to celebrate ...

The Sweetest of Sweets

From rich, smooth ice cream at Mitchell’s Ice Cream to gourmet chocolates at Campbell’s Sweets Shop, nary a romantic holiday doesn’t involve a ridiculous amount of sugar. (You won't hear us complaining.)

Get Cultured

Grab a bagged lunch, have a picnic at Wade Oval and then take in the awesomeness of University Circle. Check out of “Rose Iron Works and Art Deco," an exhibit at the Cleveland Museum of Art centered around decorative metalwork by Martin Rose. The exhibition traces Rose’s shift from Art Nouveau to Art Deco — a legacy that began when he brought his family from Hungary to Cleveland, where Rose Iron Works still thrives 120 years later. Or, catch "Refocusing Photography: China at the Millenium" for a celebration of a rebellious group of Chinese artists who broke the norm and brought photography into the spotlight in Chinese contemporary art.

Leaf Peeping

If there’s anything truly worth peeping this fall, it’s the leaves. According to the Ohio Department of Natural Resources, The Land experiences peak fall foliage colors between early- and mid-October. So take a trek through the scenic Cuyahoga Valley National Park, take your pick of trails within the Cleveland Metroparks, stroll among the gardens at the Cleveland Botanical Garden or get a breathtaking view at Holden Arboretum.

Beer Me, Babe

For many of us — especially in Cleveland — Cupid’s arrow doesn’t come from a satchel, but rather a growler he wears strapped to his back. If the way to your heart is through a frosty craft beer, pick up some cold ones or grab patio seating at places like Great Lakes Brewing Company, Collision Bend Brewing Company, Market Garden Brewery and countless others. Why not get started on our newest edition of our Brewery Passport and earn prizes while you're at it?

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