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Harvest Festival Vendor Registration is Closed.

Welcome to the Home of the

Headland Chamber of Commerce

Headland is the Gem of the Wiregrass and the Headland Area Chamber of Commerce makes it our mission to share with our community and guests the details of what makes Headland so special. Our business community comes together to support and enrich our community. We host events all year to create a strong sense of place and simultaneously impact our economy. Experience the Good Life centered on our beautiful square in Headland.

Mark Your Calendar

We invite you to enjoy our festivals and events in Headland's own front yard. Our downtown square is at the center of almost everything we do. Take note of our Headland After Hours events and other things throughout the year!

Under the Oaks

Under the Oaks is back! Headland welcomes you to shop, dine and listen to the musical artists we have this year.
Save the Dates!
April 19th
May 17th
June 21st
July 19th


Harvest Festival 2024

Harvest Festival 2024 will be October 11-12, 2024. We are looking forward to another fun-filled weekend of arts and crafts, music, food, 5k, car and tractor shows, and more!



Headland Chamber Blog

Hear the latest Headland News from our team! Get insights into events, celebrations and behind the scenes in the Chamber.

Farmers Market

Headland Farmers Market Opens May 31st

By | May 13, 2024

Headland Farmers Market is back! Join us on the Square in Downtown Headland every Friday from May 31st to July…

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Women in Business Flier

By | March 22, 2024

We are extremely excited about a new event this year, our Women in Business Brunch! As many of you have…

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Under the oaks, Date Night

Under the Oaks 2024

By | March 10, 2024

It’s almost that time once again! Under the Oaks is just around the corner, and I don’t know about you,…

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