300 Oaks Road Race: Run Through the
Heart of the Delta
The 45th Annual 300 Oaks Road Race returns to Greenwood on Saturday, September 20. Hosted by the Greenwood-Leflore County Chamber of Commerce, this signature fall event is one of Mississippi’s longest running traditions. It began as a tribute to the 300 oaks planted along Grand Boulevard and continues to draw runners and walkers from across the region.
Choose Your Course
With four race options, there’s something for every pace and experience level. Whether you’re chasing a new personal record or taking a stroll with friends, the 300 Oaks experience is open to all. Start times are:
- 10K Run – 8:00 AM
- 5K Run – 8:10 AM
- 5K Walk – 8:15 AM
- 1-Mile Fun Run – 9:00 AM
The courses wind through shaded neighborhoods, along historic downtown and beside the newly revitalized Rail Spike Park trail. Designated cheer stations will keep the energy high along the way. Register solo or join a team of five or more for group discounts on the 10K or 5K Walk. All roads lead to a lively Delta afterparty between the bridges on the Yazoo River, where you’ll find burgers, cold drinks and great company. If you’re ready to race you can visit 300oaks.com to sign up and secure your spot at the starting line.
Make It a Getaway to Remember
Beat the morning rush and settle in before race day by arriving early and staying local. Greenwood offers the perfect backdrop for a fitness-filled weekend, with everything you need to rest, recharge and explore. Start your stay with a visit to The Alluvian Spa, where every treatment relaxes you. From deep tissue massages to signature Delta botanical therapies, it’s the perfect pre-race indulgence or post-run reward. Quiet lounges, plush robes and expert service make it a serene retreat before the action begins.
When it’s time to eat, Greenwood delivers bold Southern flavor with creative flair. Fan & Johnny’s reimagines regional classics with dishes that surprise and satisfy – think pimento cheese fritters, heirloom tomato salads and Delta-style duck confit. For something more casual but just as craveable, grab a plate at Drake’s BBQ, where the ribs are slow smoked and the sides are made from scratch. We make sure you won’t leave hungry.
Stay and Stray
Greenwood isn’t just a destination – it’s your home base for exploring the Delta. Let the weekend unfold with a journey through blues history and cultural landmarks. Use our Interactive Map to guide your way through legendary music sites, roadside eats and scenic stretches that capture the rhythm of the region. Pro Tip: Listen to our curated Spotify blues playlist as you stray.
Lace Up and Join Us
The 300 Oaks Road Race is more than a run. It’s a Delta tradition rooted in movement, music and community. Find Your Beat from the Heart of the Delta and turn race day into a full getaway. Book your stay now and experience everything Greenwood has to offer – before, during and after the finish line.