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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.
This year we have a great lineup:
April- The Ryan Waters Band
May- The Rock Mob
June- The Park Band
July- The Velcro Pygmies


Headland Harvest Festival

You don't want to miss the 52nd Annual Harvest Day brought to you by HNB First Bank and Hometown Food Center and Willy D's, Friday October 13 - Saturday, October 14th. The day is a tribute to local farmers and the harvest season. It includes a car show sponsored by HNB First and Hometown Foods, children’s games and rides, arts and crafts, food vendors and live entertainment throughout the day.


Headland Chamber Blog

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

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Cookie Crawl!

By | November 1, 2023

Cookie Crawl This year during Sundown Cinema we’re having a Cookie Crawl! Come down to the Square to join in…

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Harvest Festival 2023

By | October 19, 2023

The 2023 Harvest Festival was a big success! We welcomed thousands of smiling faces to our downtown to enjoy fair…

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August Chamber News

By | August 21, 2023

August Chamber News  It’s Back to School time already! I hope you all enjoyed your Summer and were able to…

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