The Bootleggers’ Run – A Notorious Rally Through Wairarapa!

Listen up, you hooch-hustlin’, backroad-burnin’, gin-lovin’ troublemakers—there’s a new event in town, and it’s got your name all over it. Introducing The Bootleggers’ Run, a high-spirited (literally) car rally through Wairarapa’s finest gin joints, wineries, and historic watering holes.

What’s the Gig?

Inspired by the roaring days of prohibition, when bootleggers smuggled their finest liquor across borders, The Bootleggers’ Run is a one-day motoring adventure packed with exclusive drink deals, vintage vibes, and a whole lotta mischief.

Your Bootleggers’ Passport is your golden ticket to:

Special hooch discounts at every participating venue

Car judging & prize-giving for the best wheels on the run

A legendary post-run shindig at The White SwanHotel

Bragging rights as South Wairarapa’s slickest liquor runner

Tweed Up, Bootleggers!

Now, we know what you’re thinkin’—bootleggers wore fedoras, pinstripes, and sharp suits, right? Well, this ain’t just any smuggling operation; were celebrating the Country Village Heaven HOOTENANNY. That means we’re running hooch in style—tweed style. Think whiskey baron meets countryside outlaw, and you’re on the right track.

Our Most Wanted List will feature the best-dressed crew—so suit up, tweed up, and show us how a real bootlegger does business.

The Route & The Rules

This ain’t a race, pa and it certainly aint about drinkin’ booze while out on the road —it’s about style, swagger, and the spirit of adventure. You’ll follow a contraband map, making stops at historic pubs, distilleries, and wineries with exclusive hooch deals just for our gang to take home. But watch out—each stop has a tight time window before the law (or just the next venue’s bartender) catches on.

At the end of the day, we’ll gather at The White Swan Hotel for prize-giving, tall tales, and a toast to a successful smuggling operation.

Sign Up or Get Left in the Dust!

Entry is $10 per car—so grab your crew, shine up your ride, and pre-register NOW to secure your Bootleggers’ Passport. No passport, no hooch deals, no exceptions.

All proceeds go to Life Flight Trust, so while we’re runnin’ booze for fun, we’re helpin’ a damn good cause.

So what d’ya say, pal? You in? Get all the details here

Register now and join the most notorious rally in the land!

Rosie Rogers