Whiskey Pines wears its charm like an embroidered cardigan; quaint, cozy, and just a little too perfect. But like most small towns, its real story is stitched beneath the surface, where the threads get tangled and the fabric starts to fray.
Most people know us as a sleepy lakeside village with good pie, a clean marina, and a suspiciously competitive quilting club. But if you know where to look, and you know who to ask, you’ll uncover a different side of Whiskey Pines. One that involves trapdoors, tunnels, and more than a few questionable moonshine recipes.
During Prohibition, Whiskey Pines was less “wholesome Americana” and more “Midwestern Casablanca.” The lake gave smugglers an easy route from Chicago, and our cozy hills provided just enough cover for hideouts, drop-offs, and secret speakeasies tucked behind false walls and under butcher shops. The most infamous of them? The one buried beneath what is now my very own Maxx Manor.
My grandmother, Roxanne, was a legend in that era. She ran one of the more refined joints—a speakeasy dressed up as a supper club. Red velvet booths, a piano that never rested, and cocktails with names like “Bootlegger’s Kiss” and “Foggy Lake Special.” She kept things classy. Or at least, classy enough not to draw federal attention. The Steeplepuss family, of course, ran a rival operation out of a much seedier location. Their gin was cheaper, their methods rougher, and their reputation just as earned as it was feared.
The two operations clashed more than once. Roxanne’s barmaid, a fiery woman named Mackenzie, now reincarnated as my very sassy Bichon, once broke a bottle over a Steeplepuss lackey’s head. That little tidbit didn’t make it into the official town records, but I’ve got the broken bottle in a shadow box to prove it.
By the time Prohibition ended, most of the tunnels had been sealed, and the stories conveniently forgotten. The speakeasies became basements, the liquor stashes turned to dust, and the secrets settled into the soil. Or so everyone thought.
Today, the only thing people smuggle around here is extra frosting on Becky’s cinnamon rolls. But if you walk through the older parts of town, you can still see hints of what came before. Look at the mismatched bricks near the bakery’s foundation. That used to be an escape hatch. Or the antique shop’s back room, May Belle swears she hears music at night when the wind is just right.
I think the past is never really gone. It just waits patiently beneath the surface, like a good recipe or a well-kept grudge. And around here, we have both.
So the next time you visit Whiskey Pines, enjoy the sugar cookies. But know they’re frosted with a little history, a little rebellion, and maybe just a pinch of contraband spirit.
Stay curious, Roxie Maxx
Descendant of moonshiners, accidental historian, and unofficial town archivist
