Under the Oaks is Brought to you by:
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Join us for Under the Oaks on the Square in Downtown Headland on the third Friday in April, May, and June, and now with a concert on the second Friday of December! This annual concert series has become extremely popular in the seven years that it's been around. Drawing concert goers from both near and far, this keystone event for the City of Headland now boasts over 12,000 attendees a year! The concert is free, all you need is a lawnchair or blanket. There are always food trucks as well as our downtown restaurants and businesses being open. Don't miss out on all the fun; everyone will be there!
Schedule of Events
April 18th - Baylee Knighton opening for The Ryan Waters Band
May 16th - The Rock Mob
June 20th - Kenny on the Keys
December 12th - TBD
Food Trucks
April 18th
Tikiz of the Wiregrass
Corndog Man
Smith Brother's
Smokin' Moe's
Mary's Grub on the Go
May 16th
Summertime Snow
Corndog Man
Smith Brother's
Sassy Southern Chics
Huey's
June 20th
Tikiz of the Wiregrass
Smith Brother's Roasted Corn
Bread for Life
Greek Street
December 12th - TBD
History of Under the Oaks
Under the Oaks music event, launched in 2019, has grown into one of the premier events in the Wiregrass area. This annual concert series takes place from April to June, featuring a wide variety of musical performances set beneath the city’s beautiful oak trees. The event offers a mix of genres from folk and jazz to rock and blues, attracting visitors from near and far. In addition to the spring and summer concerts, a special Christmas edition is held each December, bringing festive music and holiday cheer to the community. Under the Oaks continues to foster a sense of connection and celebration, showcasing talent, food vendors, and family-friendly activities in a welcoming and vibrant atmosphere.
Under the Oaks FAQs
