It will mark his 31st time to participate in the footrace.
"I missed the first one in '77," said Kennedy, age 74. "I had just started running that year and it was a six-miler. The next year I took a chance and ran it ... and I've kept running it."
Kennedy, a retired accountant living in Columbus, says his goals in the Gum Tree have changed over the years.
He's run a Gum Tree PR of 45 minutes, 8 seconds in 1981 and a slowest time of 1:32.06 in 2007.
"At first, I was just trying to run to stay healthy," he said. "Then I got fired up about winning trophies and setting PRs. Now I'm running for the fun of it.
"My goal is to run as long as I can."
Another goal of Kennedy's is run in 500 road races. This year's Gum Tree will be No. 489.
Kennedy runs between 15 and 20 miles per week with a little walking mixed in. He still participates in 10 or more races a year.
Prior to cutting back on his racing, he took up marathons. His last was the Mississippi Marathon in 2006.
"Running marathons got in my blood," said Kennedy, who qualified for and ran in three New York Marathons, the last one in 1991. "I've made a lot of friends in running over the years and at the Gum Tree."
Mike Lail, the former director of the annual Tupelo Marathon, says Kennedy was once a regular in his race.
"He's a classic; he's the real deal," Lail said.
Kennedy has seen the Gum Tree reach its peak with more than 2,000 runners in the early '90s. He's also made the 6.2-mile run through town with some of the race's smaller fields.
"Running kind of comes and goes. Not a lot of young people are running these days," said Kennedy who runs for the Golden Triangle Running and Cycling Club. "I like the Gum Tree. It's still a great run."