Keith Baylor of Baylor Melons Credit: Lloyd Degrane

At least once a week all summer long someone in the Baylor family drives down south and hauls back a 48-foot semitrailer filled—front to back, top to bottom—with sweet, crisp, 90-percent-water-based nostalgia.

It could be 23-year-old Jeremy Baylor, or his 30-year-old cousin Keith, but more often it’s one of their fathers—brothers Homer and Mack, respectively—who makes the watermelon run. They deliver their load to the family’s market at Halsted and 101st, and then various relatives fan out with smaller trucks, piled high with bright green-and-white-striped globes and oblongs. You might have spotted them, parked somewhere on the south side, perhaps along Stony Island or 95th Street. Keith or Jeremy, or their cousins or family friends, sit up in the truck bed all day long, weighing and pricing fruit, slicing off samples, and making change for customers.

Many of the customers are of Homer and Mack’s generation, and were raised, as the brothers were, in the south. Maybe their own parents grew and sold watermelons.”We fulfill a demand for something that reminds people of the south, before they all migrated north to find factory jobs,” says Keith.

Homer and Mack, both in their 60s, were born in central Mississippi in a town called Hickory, along with their older brothers Lieutenant and Elton. In 1953 their father, Hezekiah “Papa” Baylor, began hauling melons north and setting up on the street in Gary. “They were one of the largest cattle farmers in the area, and they grew watermelons kind of on the side,” says Keith. “They picked cotton and worked in the fields, and they would bring the watermelons north in the summertime, before 57 was even a highway.”

Over the years they added regular stops in Chicago and Milwaukee, staying for a day in each before turning around and heading back home. In the mid-1960s Hezekiah’s sons began moving one by one to Milwaukee, where watermelon sales became an infrequent sideline to construction work for a time. Mack, who’s 62 and the youngest of the four brothers, made his way to Milwaukee in 1966. He worked there for a few years until he bought his first semi, a GMC with two gear shifts and a gutted muffler. Now the brothers and their sons use their own trucks to haul steel and other freight around the midwest when watermelon’s not in season.

The family tapped into a network of farmers across the south, and beginning each May collected their first load from Florida and made the two-day trip north, sleeping in their cabs. Keith says his father Mack tells the story of coming down the steep incline of Monteagle Mountain in Tennessee, an infamous stretch of Interstate 24 just over the Georgia border, and having to take both hands off the wheel to downshift. His muffler announced his arrival up to three miles off.

In 1971 the brothers opened their first permanent seasonal watermelon market in Milwaukee—now there are three—and in the early 80s Homer opened the red cinder-block market at 101st and Halsted that serves as the Baylors’ Chicago HQ. Jeremy mostly runs it now.

Keith grew up in Milwaukee selling melons, and later roasted peanuts, too, in the markets and on the trucks. Watermelons helped put him through Howard University, where he studied business. But the allure of the road and the loyalty of his customers brought him back to the trucks. He has a wife back home whom he doesn’t get to see much during melon season.

The Baylors used to rely just on word of mouth from their regulars to get the news of their locations out, but Keith recently set up a Twitter account, @baylormelons. They don’t have a website or even a phone number, though you can always ask at the Halsted market, open 8 AM to 9 PM daily. For five years running they’ve attracted a dedicated following among the food enthusiasts at LTHForum, who keep track of the arrival and changing locations of the trucks. Posters have noted the complex and subtle flavors of the watermelons and have speculated that the fruits take on “herbal” and “grassy” notes from crops in surrounding fields.

“I don’t know where people pick up on that,” says Keith, who eats watermelon every day for breakfast. But he does agree they are superior to store-bought melons—they’re fresher, sweeter, and crisper, and for that he sells each individually weighed melon at a constantly changing premium. In early June the Florida melons were selling from $7 to $12 for 18 to 45 pounds. Compare that to 15-pound Texas watermelons on sale at the same time for $4.99 at Cermak Produce.

Lieutenant and Elton are now retired—other family members operate the Milwaukee trucks and markets. “My dad will go get a load and we’ll switch trailers. We might trade up, it all depends on the situation, like if I still have melons here, my dad will go get them. Or he might stay here and sell, or I will go get the load,” Keith says.

They follow the melon crop north as the season advances. After Florida, they get them from Georgia, and then around July 4 they’re selling the prized Mississippi melons, which benefit, says Keith, from the region’s red clay soil. “A lot of our customers are from Mississippi, so we try to get Mississppi product. That’s the way we’ve survived over the years.”

Keith Baylor says this week, in addition to the red seeded and seedless watermelons, he’ll be selling yellow-fleshed watermelons from Mississippi. E-mail him at