The Skip Button Won. Here’s the One Ad It Never Touched.
Consumers have spent twenty years building an escape hatch out of advertising. Billboards are the only medium that never gave them one, and the data shows why that matters.
News
The Anatomy of a High-Impact Billboard: Design Principles That Actually Work
A driver on I-59 outside Laurel is closing on your billboard at roughly 70 miles per hour. That gives them
Billboards Are Dead? The Numbers Tell a Very Different Story
Every few years, someone declares out-of-home advertising obsolete. The data keeps refusing to cooperate. Here is what the numbers actually say about billboards in 2026.
Billboard Advertising in Philadelphia, Mississippi
Philadelphia, Mississippi Trailhead Media Philadelphia, the seat of Neshoba County, took its current name in 1903, two years before the
Billboard Advertising in Louisville, Mississippi
Louisville, Mississippi Trailhead Media Louisville is the seat of Winston County in east-central Mississippi, a community that describes itself as
Billboard Advertising in Seneca, South Carolina
Seneca, South Carolina Trailhead Media Seneca, in South Carolina’s Upstate, was founded in 1873 as a railroad town and has
Billboard Advertising in Spartanburg, South Carolina
Spartanburg, South Carolina Trailhead Media Spartanburg is one of the anchor cities of South Carolina’s Upstate, with an active downtown
Billboard Advertising in Jesup, Georgia
Jesup, Georgia Trailhead Media Jesup, the seat of Wayne County, grew up around a set of railroad junctions in the
Billboard Advertising in Cartersville, Georgia
Cartersville, Georgia Trailhead Media Cartersville, the seat of Bartow County, sits 45 miles northwest of Atlanta directly on I-75, spanning
Billboard Advertising in Waycross, Georgia
Waycross, Georgia Trailhead Media Waycross, the seat of Ware County, earned its name honestly: six rail lines converge in the
Billboard Advertising in Adel, Georgia
Adel, Georgia Trailhead Media Adel is the seat of Cook County, Georgia, sitting directly on I-75 between Tifton and Valdosta.
Billboard Advertising in Monroe & West Monroe, Louisiana
Monroe & West Monroe, Louisiana Trailhead Media Monroe and West Monroe, Louisiana, sit on opposite banks of the Ouachita River
Billboard Advertising in Panama City, Florida
Panama City, Florida Trailhead Media Panama City, Florida, on the Gulf Coast in the Florida Panhandle, is Trailhead Media’s primary
Billboard Advertising in Paducah, Kentucky
Paducah, Kentucky Trailhead Media Paducah, Kentucky, sits at the confluence of the Ohio and Tennessee Rivers in the far western
Billboard Advertising in Lewisburg, Tennessee
Lewisburg, Tennessee Trailhead Media Lewisburg, Tennessee, the seat of Marshall County, is one of Trailhead Media’s most concentrated billboard markets
Billboard Advertising in Pearl & Brandon, Mississippi
Pearl & Brandon, Mississippi Trailhead Media Pearl and Brandon, Mississippi, sit just across the Pearl River from downtown Jackson, and
Billboard Advertising in Anniston & Oxford, Alabama
Anniston & Oxford, Alabama Trailhead Media The Anniston-Oxford-Jacksonville corridor in Calhoun County is Trailhead Media’s single largest concentration of billboard
Billboard Advertising in Greenwood, South Carolina
Greenwood, South Carolina Trailhead Media Greenwood, South Carolina, in the state’s Lakelands region, is one of Trailhead Media’s most concentrated
Billboard Advertising in Tifton, Georgia
Tifton, Georgia Trailhead Media Tifton sits at the junction of I-75 and US-82 in South Georgia, and it’s one of
Let’s Talk About What Billboards Are Actually Worth
Every advertiser eventually asks the same question: how does a billboard actually compare to the other places I could put
The Real Reason Trailhead Media’s Growth Worked: The People, Not the Playbook
Trailhead Media’s story is easy to summarize in numbers: 46 acquisitions, nine states, more than 3,300 billboard faces, built from
The Trailhead Model Looked Simple on Paper. Building It Was Not.
The way Trailhead Media describes itself in a press release is simple: acquire fragmented rural billboard operators and run them
Lessons From 46 Billboard Acquisitions in Five Years
Trailhead Media’s growth story is often told in numbers — 46 acquisitions, nine states, more than 3,300 billboard faces in
Where the Out-of-Home Industry Is Headed Next, According to Trailhead’s CEO
Trailhead Media CEO John Murrow started his out-of-home career in 2005 as a real estate representative in Charleston, South Carolina,
What Out-of-Home Advertising Still Gets Wrong About Customers
After two decades in out-of-home advertising, Trailhead Media CEO John Murrow has a clear view of where the industry loses
The Acquisition Checklist Trailhead’s CEO Built From 46 Billboard Deals
Trailhead Media has closed 46 acquisitions in under five years, growing from zero to a nine-state billboard network. Along the
How Trailhead Media Was Built to Buy the Billboards No One Else Wanted
When Trailhead Media co-founder and CEO John Murrow looks back at 2020, the opportunity he saw wasn’t glamorous. It was
Trailhead Media Partners with Little Creek Landing and Safari in Sumrall, Mississippi
Trailhead Media is proud to support Little Creek Landing and Safari, an outdoor adventure and family-friendly destination in Sumrall, Mississippi,
New Digital Billboard Now Live in Carthage, Mississippi
Trailhead Media has added a new digital billboard in Carthage, Mississippi, expanding opportunities for local businesses and organizations to connect
Trailhead Media Completes Its Largest Sky Sign Installation
Trailhead Media has completed its largest sky sign installation to date, a landmark structure built in partnership with Alabama Power
New Billboard Structure Coming to Jacksonville, Alabama
Trailhead Media is expanding its presence in Jacksonville, Alabama, with a brand-new billboard structure set to go live in the
Trailhead Media Celebrates Six Years
Trailhead Media recently marked six years since its founding — a milestone the company spent reflecting on how far it
A Brief History of Out-of-Home Advertising
Out-of-home advertising has a track record almost no other medium can claim: it was here before radio, before television, and
The Most Unforgettable Billboards in Advertising History
The best billboards don’t just sell — they lodge in memory and refuse to leave. Campaigns That Became Icons Chick-fil-A’s
Digital vs. Static Billboards: Separating the Hype from the Reality
Digital out-of-home is one of the most exciting developments in the billboard industry — and also one of the most
The Spartan Outdoor Story: Lon Hatcher’s Billboard Legacy in Spartanburg
Spartanburg, South Carolina sits at a crossroads of Upstate commerce, and for years, some of its most visible advertising real
The Leslie Outdoor Story: Three Decades of Billboard Building in Middle Georgia
Few people know the middle Georgia billboard market as well as John Leslie. By the time Leslie Outdoor joined Trailhead
The Cox Media Story: Kerry Cox and the Roots of Trailhead’s South Carolina Network
Every billboard company has a founding story, and for Trailhead Media, one of the first chapters was written in Easley,
Trailhead Media Partners with Christian Aid Ministries
Trailhead Media expanded its partnership with Christian Aid Ministries (CAM) in 2026, dedicating billboard space across its nine-state Southeast network
Trailhead Media and Formetco Celebrate 300th Digital Billboard
Trailhead Media and display manufacturer Formetco marked a major milestone in 2025: the installation of Trailhead’s 300th digital billboard face,
Trailhead Media Reaches 44 Acquisitions Since Founding
By the end of 2024, Trailhead Media had completed 44 acquisitions since its founding in 2020, growing into a network
40 Acquisitions in 3 Years: Trailhead Media’s Rapid Growth Story
When Trailhead Media started on July 8, 2020, it had no employees and no assets. Three and a half years
Trailhead Media Acquires Billboards for Education in Tennessee and Georgia
Trailhead Media expanded its Tennessee and northern Georgia footprint in early 2023 with the acquisition of Billboards for Education, adding
Randy Otto Named President and CEO of Trailhead Media
Trailhead Media named Randy Otto President and CEO in 2022, bringing 46 years of out-of-home industry experience to the growing
Trailhead Media Continues to Grow Across the Southeast
Within its first year, Trailhead Media had already grown into one of the largest bulletin and poster companies in the
Trailhead Media Acquires InSite MediaCom’s Georgia and South Carolina Billboard Network
In one of its largest early deals, Trailhead Media acquired InSite MediaCom’s billboard operations in October 2020, adding 1,271 advertising
How Many Words Should a Billboard Have, and Why Less Is More
If you are planning your first billboard, the question of how many words to use often comes up before the
What Is Out-of-Home Advertising and How Does It Work
Out-of-home advertising, often shortened to OOH, is one of the oldest forms of advertising and still one of the most
Static vs Digital Billboards: Which One Works Better for Your Business
If you are planning your first outdoor advertising campaign, one of the earliest decisions you will face is static vs
The Complete Guide to Outdoor Advertising for Local Businesses
When most people think about growing a local business, they think about a website, social media, and maybe some paid
Company News
Announcements on Trailhead Media’s growth, acquisitions, and leadership — posted as new deals close.