In the shadow of the roaring twenties, when jazz poured out of radios and the law poured no liquor, the Seaboard Air Line Railroad cut its way through the heart of the South — from Richmond to Raleigh, from Pinehurst to Savannah. Its freight yards were the veins of Southern commerce, but tucked between the barrels and crates were secrets of a different kind.

One of those secrets lived right here — in the Southern Pines Freight Building, now home to The Seaboard Speakeasy.

As Prohibition tightened its grip, the rail lines became lifelines for the thirsty. The trains themselves were innocent enough, but the men who loaded and unloaded them — the warehouse clerks, the night watchmen, the freight handlers — they saw opportunity rolling by on steel wheels.

Legend has it that the Southern Pines stop was a key waystation on a quiet underground network known among the railroad men as “the Bootleggers’ Line.” They ran a clever system:
- Barrels of cheese from Wisconsin arrived heavy — but never quite the right weight. Beneath the waxed rounds, mason jars of corn liquor nestled like hidden treasure.
- Suitcases shipped from New York to Savannah came double-walled — shirts and slacks on top, rye whiskey below.
- And when the train stopped late at night, miles from any depot, it wasn’t a schedule error. It was a handoff — crates sliding from railcar to wagon under moonlight, heading to secret rooms like this one.

It’s said that inside this very freight building, one particular storage room — thick brick walls, cool air, and one steel door — was used to stash contraband until the next train south. The clerks knew to keep the door locked and the books clean. The foreman was rumored to look the other way — for a share, of course.

And when the night trains slowed along the pine-lined rails, a faint melody of piano and laughter was sometimes heard drifting through the slatted doors. Maybe it was just the wind. Or maybe it was the earliest echoes of what this place was always meant to be — a haven for music, for mischief, and for those who lived life between the lines.

When Prohibition ended, the bootleggers vanished, the liquor flowed freely, and the freight building went quiet again. For nearly a century, it sat in waiting — its bricks holding whispers of clinking bottles and soft jazz through the walls.

Now, a hundred years later, The Seaboard Speakeasy reclaims that spirit. Where once the freight men stacked crates of contraband, guests now gather over craft cocktails and candlelight. The piano plays again. The laughter returns. And the legend — long buried under dust and time — lives on.