Trailhead Media

Trailhead Media is an out-of-home advertising company headquartered in Laurel, Mississippi, that owns and operates static and digital billboards across the southeastern United States. Founded in 2020, the company has grown primarily through acquisition, completing 44 deals through 2024. Its early expansion included the purchase of Busby Outdoor assets, followed by transactions with operators such as Cox Media and Spartan Outdoor Advertising, with sixteen operators acquired in 2021, seven in 2022, and thirteen in 2023. Trailhead Media now serves nine states: Alabama, Florida, Georgia, Kentucky, Louisiana, Mississippi, North Carolina, South Carolina, and Tennessee.

The company markets a network of billboard faces aimed at local, regional, and national advertisers seeking high-visibility outdoor placements. Its offering spans traditional printed bulletins and posters alongside digital displays, and it runs digital conversion initiatives that replace printed structures with electronic screens. Trailhead Media describes itself as customer-focused and quality-obsessed, and states that it plans to invest more than 20 million dollars over two years in network expansion, inventory upgrades, structural and lighting improvements, and printed-to-digital conversions. The company reports that a portion of its digital displays have received replacements, upgrades, or technology improvements as part of this program.

Its network of billboard faces is marketed to local, regional, and national advertisers seeking high-visibility roadside exposure across the southeast. Trailhead Media is a member of the Out of Home Advertising Association of America and Geopath, the industry organizations for outdoor media standards and audience measurement, reflecting participation in recognized measurement and reporting practices.