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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.

May News

By | May 9, 2023

Happy May, and happy last month before summer is officially kicked off! We had a blast with you guys at…

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Under the Oaks event with crowds in a park

April News

By | April 14, 2023

Spring has officially sprung here in Headland, and with southeast Alabama weather you don’t know what you will get! We…

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Gemmy Award Winners!

By | February 14, 2023

Hey Headland! We have exciting things happening in March. Come out to HHS Auditorium for Miss Headland on March 4th…

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