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 networking events throughout the year as well!

Your Face Tells Your Story

Tuesday, April 1

11AM - 1PM

Join us at the TLC Photography Studio in Headland for this special networking event!

Admission comes with one headshot picture, lunch from The Rollin' Trapp food truck, and the opportunity to network with some of the best people around! Members pay only $25 for a ticket and Not-yet Members pay $75. We look forward to this exciting event with you!

Buy Your Tickets Here!

Under the Oaks

Under the Oaks will be back before you know it! Headland welcomes you to shop, dine and listen to the musical artists we have this year.

Save the Dates!
April 18th
May 16th
June 20th
December 12th

Get the Details

Upcoming Events

View All Upcoming Events

Experience the Good Life

Welcome to the Gem of the Wiregrass!

We are proud to release our first issue of our Headland Magazine. Headland has a lot to celebrate. We encourage you to take a moment to explore what makes our community so loved.

Community Guide:
Check out the 2025 Headland Magazine & Business Directory for information on the wonderful attractions and amazing treasures in the Headland community along with the Chamber Member directory, an easy way to find a business for all of your needs.