Meet Kenny “The Watermelon Man” Smith: A Sweet South Side Legend

The South Side Summer Scene

On summer evenings at 83rd Street and Stony Island Avenue, Kenny “The Watermelon Man” Smith is a fixture—his truck loaded with perfectly ripe melons, drawing crowds of loyal customers and curious passersby. For nearly two decades, he’s brought red, yellow, and even orange watermelons—plus peaches, pecans, and southern produce—to Chicago’s South Side from farms all across the South.

Craft, sourcing, and standards

Smith’s business is rooted in tradition and expertise. Each week, he drives thousands of miles to handpick the freshest fruit directly from farmers he’s trusted for years. He stands behind his product, proudly telling customers they won’t find this quality—or sweetness—at any grocery store. “If they come over here, they’re going to get a good watermelon,” he insists.

Legacy and culinary influence

Beyond sales, The Watermelon Man represents a lineage of Black entrepreneurship stretching back to Reconstruction, when growing and selling watermelons was both survival and pride. Despite negative stereotypes, Smith and peers continue this legacy, bringing healthy, fresh food and positive community presence to Chicago. Inspired by Smith and his produce, local food innovators like Chef Maya-Camille Broussard of Justice of the Pies incorporate his melons into new recipes, “reclaiming the positive attributes of watermelon” for a new generation.

Family, future, and access

Smith’s operation is also a family affair, with his son learning every facet of the business since childhood. His dream is to one day open a permanent storefront on Stony Island, offering affordable fresh produce and accepting SNAP benefits—ensuring healthy choices for every neighbor.

Set in stone on Stony Island

For many South Side residents, summer isn’t complete without a visit to The Watermelon Man’s truck. Longtime fans rave, “I haven’t gotten a bad one from here yet.” Smith’s presence is part of the fabric of the community, and he hopes to remain “set in stone on Stony Island,” serving up sweetness and southern hospitality, one melon at a time.

Support local business and tradition—catch Kenny “The Watermelon Man” Smith on Stony Island, and taste the sweetest slice of summer in Chicago.