The Headland Area Chamber of Commerce known fondly as the "Jewel of the Wiregrass " plays a role, in enhancing the Headland community in Alabama. The Chambers's main focus is on supporting businesses creating a business environment and strengthening the economic and social fabric of the region. Membership perks include opportunities for networking, access to business resources, and increased visibility all geared towards promoting business growth and community progress.

The Chamber is well known for its range of events that cater to both businesses and the general public. Among these events, the Gemmy Awards stand out as a celebration that honors exceptional local businesses, individuals, and community contributors. These events along with activities like business mixers, workshops, and festive gatherings not facilitate business connections. Also foster a strong sense of community, in Headland.

Becoming a member of the Headland Area Chamber of Commerce means joining a network committed to advancing businesses and nurturing a united community spirit. Through its events, the Chamber offers platforms for members to showcase their businesses interact with peers, and contribute to the growth of the community. Making Headland a place to reside work in and conduct business.