The Bootleggers’ Car Run ain’t for Sunday drivers! We’re cruisin’ the hills and valleys, makin’ secret pickups at wineries, gin joints, and historic hideouts. Your contraband map will guide you to the best deals, but ya better move fast—each stop’s got a tight window before the fuzz catches wind, its’s a race against the law—metaphorically, of course (we ain’t lookin’ for trouble).

Think your ride’s got class? Our top booze barons will be judgin’ the finest wheels on the road, with the big reveal at The White Swan Hotel Bootleggers’ Mingle from 3.30pm onwards. The best-dressed crews and finest-looking motors might just land themselves on the Most Wanted list… for all the right reasons.

So shine up your bumpers, grease those tires, and keep your flask handy—we got one rule in this game: Full yah Boots!

In collaboration with the Country Village Heaven HOOTENANNY, on Saturday 26th April 2025 we have amassed a collection of Wairarapa finest Wineries’, Distillers’ and Breweries’ to offer you an opportunity to FILL YAH BOOTS (and your grog cabinet at home). 

Registrations are $10 per car (all proceeds go to Life Flight Trust). Let us know how many passengers will hitch a ride when you register (you all get the deals).

It ain’t just about the cars—you gotta look the part. The most notorious bootleggers in history weren’t just outlaws; they were dressed to kill. Prizes to be won folks so get slick.

This ain’t just a drive—it’s a roaring prohibition road trip! So rev up, dress sharp, and let’s run some hooch!

ITINERARY

1.The Contraband Passport Collection

Your Passport to Prohibition Perks!

Collect your passport (and have a coffee) 9.30AM - 11AM - The White Swan Hotel, Greytown

Every good bootlegger needs a stash spot, and yours is a contraband passport filled with exclusive hooch vouchers. At each stop, you’ll be collecting liquid loot—from fine wines to top-shelf gin—just like the old-time runners did, minus the feds breathin’ down your neck. But don’t dawdle! Each deal’s got a tight time window (or cellar door opening time), and only the sharpest smugglers get their hands on the best stock.

Cars MUST Be pre registered (REGISTER NOW)  to gain a Bootleggers’ Passport. $10 per car, let us know how many passengers ya got when you register!

Think you got what it takes to join The Bootleggers’ Car Run? Then ya better pre-register NOW to secure your Bootleggers’ Passport—no passport, no hooch deals, no exceptions.

• Entry Fee: $10 per car (don’t forget to declare how many crew members you’re smuggling… so they can all get the deals!)

• Your Passport grants you:

• Exclusive discounts at every speakeasy, gin joint, and watering hole along the route.

• Eligibility for judging & prize-giving—think your getaway car is the slickest in the gang? Prove it.

• Access to the post-run shindig at The White Swan, where the best of the best will be crowned.

All proceeds go to Life Flight Trust, helping them keep up their life-saving work—because even bootleggers look out for their own. Get registered or get left in the dust!

2.The speakeasy circut

Visit Wairarapa’s Finest (and Most Notorious) Joints as well as some back road gems you won’t see in the big smoke.

10am - 3.30pm - Pay attention to the cellar door opening times when planning your route of choice.

No bootlegger worth their salt, runs empty roads! Your route is packed with top-tier speakeasies and backroom bars, from the historic White Swan Hotel to the finest gin distilleries and wineries in the region. Each stop has a special “off-the-record” deal just for our crew—just flash your passport, mumble the secret words (“I’m Bootleggin’”), and you’ll get the good stuff at a price only a wise guy could love.

You’re free to roam as you please, just make sure you cross through Checkpoint Charlie between 11am - 1.30pm to be judged if you want to be considered for a prize! More insider info on that below.

3.Checkpoint Charlie

Who’s Got the ‘Slickest Ride’ and ‘The Most Wanted’ Awards

Make sure you pass through Checkpoint Charlie between 11am - 1.30pm, give our judges a subtle nod for a prize.

Whether you’re runnin’ a vintage hot rod, a classic cruiser, or a modern-day getaway machine, you’ll want it lookin’ sharp for the big judging showdown. Our most feared and respected hooch inspectors will be eyeballin’ every ride, lookin’ for style, swagger, and straight-up outlaw attitude. Winners get crowned at The White Swan Bootleggers Mingle, with braggin’ rights (and maybe a little extra liquid gold) up for grabs.

4. THE dressCODE

Bootleggers didn’t just run hooch—they ran in style. And since we’re celebrating the Country Village Heaven HOOTENANNY this ain’t just any backroad smuggling operation—it’s a high-class, tweed-clad, prohibition-era affair.

Think of yourself as a distinguished liquor baron, a dapper gin-runner, or a tweed-covered troublemaker. Whether you roll up lookin’ like a whiskey tycoon, a countryside smuggler, or the sharpest-dressed outlaw this side of the Rimutakas, our judges will be on the lookout for the most dapper crew.

So button up, buckle in, and show us how a real bootlegger brings the goods—in tweed!

5. THE LOOT

• Best Classic Car – pre 2000 – Win a Midweek Deluxe One Night Package at the White Swan Hotel, Greytown.

• Best Contemporary Car – Post 2000 - Midweek Deluxe One Night Package at the White Swan Hotel, Greytown.

• Best Dressed (Tweed) - Win a $250 Voucher to The White Swan Hotel, Greytown.

• The Star of the Show – Win a Midweek 2 Night Deluxe Package at the White Swan Hotel, Greytown.

6. The bootleggers’ mingle

A Last Toast at The White Swan - 3.30pm onwards

After a long day of running hooch and dodgin’ imaginary roadblocks, we all land back at The White Swan Hotel for the big reveal. This is where we crown the best cars, best-dressed crews, and top-tier bootleggers of the day. The last bottles get emptied, the last deals get made, and everyone walks away a little richer in spirit.

THE CONTRABAND MAP

Your contraband map will guide you to the best deals, but ya better move fast—each stop’s got a tight window before the fuzz catches wind. Go in any direction you please.

The deals will be vaild for one special day only.

BOOTLEGGERS’ BACKROAD HIDEOUTS

Even the best hooch runners need a place to lay low between liquor stops. We’ve marked some hidden backroad gems where you can catch your breath, stretch your legs, and soak up a little scenery before your next pickup.

1. 447 Admiral Road– A giant picture frame with a view fit for a kingpin.

2. Land Girl Cafe, Pirinoa – Strong coffee, hearty bites—keep your crew fuelled.

3. The Gobbler Golf Course, Gladstone – Swing clubs, not punches. A quick round never hurt a bootlegger.

4. Olivo Olive Oil, Martinborough – Top-shelf olive oil, because not every bottle’s gotta be booze.

5. Greytown Art Gallery, Greytown – Even outlaws can appreciate a bit of fine art.

Take a detour, snap a pic, or just lay low ‘til the heat dies down.