Featured Image: Destination Panama City Florida
May in the South brings longer days, warmer nights, and calendars packed with can’t-miss events. From laid-back outdoor festivals and waterfront traditions to food-filled weekends and live music at sunset, it’s the perfect time to get out and explore. Whether you’re craving local flavor, small-town charm, or a lively crowd, these events offer a little something for every kind of spring adventure.
BirdFest | Pinewood, SC
May 1-2, 2026
Nestled between two of South Carolina’s favorite cities is a laid-back festival filled with local food trucks, live Blues bands, and the great outdoors. Affectionately named after a previous resident mule, BirdFest in Pinewood, SC brings charm and community together to a former quail farm for an annually loved tradition. Proceeds from the festival support the South Carolina Waterfowl Association’s efforts to protect wildlife and their habitats.
Blessing of the Fleet | Panama City Beach, FL
May 2, 2026
Boating season in Panama City Beach, FL gets a one-of-a-kind welcome with Blessing of the Fleet, a time-honored event that centers around the town’s connection to life on the water. Shrimp boats and sailboats gather in St. Andrew’s Marina to receive well wishes for smooth voyages ahead, as locals kick off their shoes and burn their socks… we’re not joking! In the weeks leading up to the big day, socks show up all over town until the community gathers to throw them into a communal fire, a nod to maritime culture welcoming warmer days and going barefoot.
The Burger Benefit | Dunwoody, GA
May 3, 2026
Come one, come all, and come hungry! The Burger Benefit in Dunwoody, GA attracts chefs from around the country who serve up their best burgers in a flavorful frenzy at designated timeslots throughout the day. This event not only tastes good but feels good too, benefitting Giving Kitchen, a nonprofit that steps up for food service workers in need of emergency assistance.
Wild About Shelbyville Arts and Music Festival | Shelbyville, KY
May 9, 2026
For the fifth year, Wild About Shelbyville Arts and Music Festival will turn downtown Shelbyville, KY into a lively showcase of local creative talent. The streets fill with live music, art vendors, and hand-on things to do with the family for a day of vibrant energy. Shop, dance, dine, and even catch a few historical re-enactments at this annual one-day event.
Canton Flea Market Arts and Crafts Show | Canton, MS
May 14, 2026
Enter an open-air marketplace across historic downtown Canton, MS as the famous Canton Flea Market Arts and Crafts Show draws visitors and vendors from all around the region. Expect a variety of unique handcrafted crafts, from pottery to jewelry to art, from hundreds of different makers at one of the largest art markets in the South. As the beautiful backdrop of the town serves as the venue, you’ll shop alongside landmarks like the Old Jail Museum and the grounds of the Madison County Courthouse.
Hattiesburg Craft Beer Festival | Hattiesburg, MS
May 16, 2026
It’s time to raise a glass, and have a tasting or several, at the Hattiesburg Craft Beer Festival in Hattiesburg, MS. All the makings of an amazing beer festival can be found here, including independent brewers, top rated food trucks, and yard games like cornhole. Whether you’re a beer connoisseur or a casual sipper, this spring day out is sure to please.
Baton Rouge Soul Food Festival | Baton Rouge, LA
May 23-24, 2026
A true celebration of Southern flavor and soul takes over Baton Rouge, LA for one indulgent weekend full of recipes that have been shared across generations. The Baton Rouge Soul Food Festival is your chance to sample some of the best comfort dishes like fried catfish, mac and cheese, and gumbo, while also witnessing a spirited cooking competition across multiple categories. The soundtrack of the day will be a combination of gospel, jazz, blues, and R&B live performances, balanced by the opportunity to browse vendors, connect with community organizations, and check out the family-friendly activities.
Symphony at Sunset | Vicksburg, MS
May 23, 2026
Make Memorial Day Weekend unforgettable with an outdoor orchestra performance at golden hour. Symphony at Sunset is held on a former battlefield in Vicksburg, MS in a scenic display of patriotism. Experience the Mississippi Symphony Orchestra from the comfort of your lawn chairs and picnic blankets at this Southern commemoration.
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