Getting to know the Australian Highwayman – Dan Woolley

A few centuries back, highwaymen were robbers who targeted travellers on public roads traveling on horseback. They were considered socially superior to their on-foot equivalents, and became known as the “gentlemen of the road.” In Australia, we knew them as bushrangers. 

Fast forward to 2016 and the Australian Highwayman was born, albeit one that doesn’t fit the historical definition. Although Dan Woolley, the man behind the one-man, small-batch Byron Bay whisky project and one of Australia’s best-travelled and most-influential whisky ambassadors, can definitely be described as a “gentleman of the road.” 

After working as an ambassador for some of the biggest whisky brands – think Laphroig, Talisker, Glenfiddich, Monkey Shoulder, Jim Beam, and Yamazaki, to name a few – he was convinced by none other than the Godfather of Australian whisky himself to start laying down his own barrels in 2016. 

“It was Bill Lark that took me aside one day and basically said to me, ‘When are you going to stop working for these big brands and start doing it for yourself?’ That's when I started to fill my own barrels,” Woolley tells Whisky Magazine. 

“My first ever 10 batches were early 2020, and that's when I launched the brand on a wing and a prayer: if it didn't work and they didn't sell then the brand wouldn't actually take off and I would have been left with going back to working for someone else. Fortunately, the first five batches sold out in minutes online.” 

When Dan tells you whisky is much more than a career choice, you believe him, partly for the passion with which he speaks about it and partly for his willingness to share with you everything he knows. 

“I'm the only person I know that has whisky tattooed across their knuckles,” he says with a grin. “For me it's my heart, it's my soul. It's all I eat, sleep, think, drink, 24 hours a day, seven days a week.

“When I sleep I dream about whisky. For me, whisky is everything, it's not something that I clock in and clock out of, it is my everything, it's my whole life.” 

Which whiskies does Dan Woolley dream about? It turns out quite a few:

“ I do dream about Islay – Islay for me is a huge, huge, huge part of my life – and I dream about Tassie. I love Tassie, I love Islay, I love Japan and Japanese whisky and the culture of Japanese whisky bars, but obviously the most prominent dream for me is when I'm basically in my own warehouse filling or tipping barrels – that for me is my favourite thing and it's constantly in my conscious and subconscious.” 

10 years young:

This year, Highwayman is celebrating 10 years since its first barrels were filled with a number of special releases, including the first ever Australian whisky fully matured in a tequila barrel. 

According to Woolley, this experiment “exceeded all expectations and then some” and is a perfect representation of everything Highwayman stands for: pushing the boundaries of what is possible with flavour through unique casks and an extremely high level of care. 

“I've got 37 different wood types in 10 different sizes. It's constant experimentation going on and the only thing I'm searching for is flavour … When it comes to American whiskey barrels alone, I have wheated bourbon, low rye bourbon, high rye bourbon, four-grain bourbon, Tennessee whiskey, rye whiskey, bourbon maple, and I have rye maple. So there's just eight different variants of American whisky barrels alone.” 

A similar story is painted for Highwayman’s stock of four table wine, six fortified, and six-to-seven alternative casks, which, in addition to the tequila cask, also includes cognac, imperial stout, maple syrup, and coffee seasoned casks, among others. 

For most releases Dan blends a number of these casks together, and always bottles completely unfiltered at natural cask strength. 

“My whole ethos is [to make] the purest whisky in the world,” explains Woolley. “Most of the time it will be a couple of barrels married together, or barrels married together and then given second or third or even up to four extra maturations. Occasionally, maybe twice a year, I do a single cask release.” 

Highwayman has never had, nor will it ever have, a core range, and sticks to its model of a new small-batch release once a month. However, it does have a 50-50 Australian-Scotch core range blend called Treacherous Radicals, available for just $99 a bottle. 



Changing of the guard:

Speaking with Dan, the conversation naturally leads to the future of Highwayman, a project that, as cliche as it sounds, is a personal extension of himself and his life. Perhaps for this reason he is happy to share it will remain in the Woolley blood line:

“Highwayman is definitely something that I'm working towards passing down to my son,” he said. 

“He's going to be 15 soon and he has helped me work from day one … He will be taking the reins in, I would say, in less than a decade; and hopefully when he takes the reins, I can sit at home with my dog, drink whisky and sit in the rocking chair with a shotgun.” 

A fitting retirement for the Australian Highwayman.