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Headland Chamber of Commerce

Harvest Day Vendors Open May 26th

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!

Headland Harvest Festival

Harvest 2025 Graphics (Facebook Shops Ad) (1)

Join us for the Annual Headland Harvest Festival a cherished community celebration that brings together the best of local culture, entertainment, and family fun! This year’s event promises to be bigger and better than ever, with a delightful mix of activities and attractions that cater to all ages. This fun-filled event takes place downtown in and around Headland's beautiful city square on October 10th & 11th. The day is a tribute to local farmers and the harvest season. It includes a car show, tractor show, children’s games and rides, arts and crafts, food vendors, and live entertainment throughout the day.

Learn More

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.