Under the Oaks 2025
Date and Time
Friday May 16, 2025
7:00 PM - 10:00 PM CDT
Every 3rd Friday of the month from April-June and now the second Friday in December, we will have a free live concert on the Square in downtown Headland.
Location
Bring your lawn chairs and blankets and come to the Square in Downtown Headland. There are several places to dine and shop while you are down here! Our local restaurants are ready to get you food and drinks on the go and our Food Trucks too! Come out to Under the Oaks in Headland and stay a while.
Fees/Admission
This is a free event.
Description
Under the Oaks is back! Headland welcomes you to shop, dine and listen to the musical artists we have this year.
This year we have a great lineup:
May 16th - The Rock Mob
June 20th - Kenny on the Keys
December 12th - TBD
We also have some yummy food trucks coming out this year:
May
Summertime Snow
Corndog Man
Smith Brother's
Sassy Southern Chics
Huey's
June
Tikiz of the Wiregrass
Smith Brother's Roasted Corn
Bread for Life
Greek Street
December
TBD
Learn More About Downtown Headland
Get a preview of music at Under the Oaks
This year we have a great lineup:
May 16th - The Rock Mob
June 20th - Kenny on the Keys
December 12th - TBD
We also have some yummy food trucks coming out this year:
May
Summertime Snow
Corndog Man
Smith Brother's
Sassy Southern Chics
Huey's
June
Tikiz of the Wiregrass
Smith Brother's Roasted Corn
Bread for Life
Greek Street
December
TBD
Learn More About Downtown Headland
Get a preview of music at Under the Oaks
