The Greenwood-Leflore County Chamber of Commerce will host the 19th annual BBB cycling event on Saturday, August 1, 2026. The rides begin in historic downtown Greenwood, home to Viking Range Corp and major site of Milwaukee Tool. Mississippi's BIKES BLUES & BAYOUS has averaged almost 800 riders for the last 5 years and was selected as a "Southeast Tourism Society Top 20 Event Winner" for 2018, 2019 & 2021. Join us to ride the fast and flat alluvial plains of the Delta and discover "the BEST Southern Hospitality on Earth".
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.
Viking Half Marathon
10K & 5K
2/6/2027
Half @ 7:30am
5K & 10K@ 8am
Located in the heart of the fabled Mississippi Delta, the Viking Half Marathon • 10K & 5K promises Southern charm, fast times, and an unbelievable race experience. From the time you arrive in Greenwood, you can expect great local culture, an array of fabulous food, and warm Southern hospitality.
The races will begin and end in the historic Cotton Row district of Greenwood and will take you through the flat, tree-lined streets of Greenwood. Racers and spectators will love the beautiful oaks and homes lining Grand Boulevard, once named ”One of America’s 10 Most Beautiful Streets” by the U.S. Chamber of Commerce and the Garden Clubs of America.
The race course also passes by many of the site locations used in the filming of the blockbuster movie The Help, which was filmed in Greenwood in 2010. To top off the weekend, restaurants, residents, and shop owners will welcome you with special menus and activities throughout the weekend. Welcome to Greenwood, a true jewel in the Mississippi Delta.
For more information call the
Greenwood-Leflore Chamber of Commerce
at 662.453.4152