From big races to Saturday morning group runs—find road events and connect with the local endurance sports community.
300 Oaks Road Race
SEPTEMBER 19, 2026
Start Times
10k Run: 8:00am
5k Run: 8:10am
5k Walk: 8:15am
1 Mile Fun Run: 9:00am
The 46th annual 300 Oaks Road Races are one of the oldest races in Mississippi. Steeped in tradition and founded in Greenwood by the inspiration of the original 300 oak trees that were planted along Grand Boulevard decades ago, this event offers something for the entire family!
We offer a 10k run, a 5k run, a 5k walk and a one-mile fun run. Each course takes you through various areas of town, including our historic downtown area and our new RailSpike Park trail (10k), and the beautiful shaded residential streets where residents are likely to be on hand to cheer you on.
We welcome TEAMS for our 5k walk/10 Run and encourage you to organize a team of 5 or more for a team discount.
Join us for the after party at the beautiful park between the bridges on the Yazoo River near the finish line. We’ll offer up grilled hamburgers and hot dogs, chips and cold soft drinks, water, and beer.