In the heart of the Blue Mountains, The Bootlegger Bar isn’t just another bar on the strip. It’s a 160-seat, multi-space venue designed for a full night out featuring serious cocktails, low and slow BBQ, live entertainment and a rooftop that feels like you’ve stumbled onto a hidden gem. From their 20+ specialty cocktails, including standout serves like Liquid Smoke, to whiskey flights featuring the biggest range in Katoomba, The Bootlegger has built a reputation as a “what’s on” destination rather than a one-off stop.
With live acoustic sets, jazz Sundays, drag bingo and trivia nights woven into their weekly rhythm, The Bootlegger blends food, drinks and entertainment under one roof, and still manages to feel curated rather than chaotic. It’s this balance of scale and experience that sets them apart.
“We’ve always positioned The Bootlegger as more than just a place to eat or drink, it’s about the full experience.”
We sat down with owner, Kelly Walls, to unpack how they’ve evolved their booking systems to support that ambition and how Now Book It has helped streamline the operational side of delivering a high-energy, high-volume venue without sacrificing service.
The hidden cost of disconnected systems
Running a venue with multiple spaces, entertainment programming and diverse dining options is operationally complex. Before moving to Now Book It, one of The Bootlegger’s biggest pain points was fragmentation.
Bookings, POS, rostering and events were operating in separate systems, creating double-handling, manual entry and avoidable errors.
Guest details were being retyped, dietary notes were copied across platforms and deposits and minimum spends for functions were tracked in different places. When last-minute changes happened, and in hospitality they always do, updates didn’t always flow everywhere they needed to.
“The biggest frustration was that nothing was truly connected, we were re-entering information, chasing confirmation emails, cross-checking notes between platforms. It’s time you just don’t have when you’re running a busy service,” Kelly said.
Last-minute cancellations and changes to guest numbers created additional strain. If a booking time shifted or numbers dropped, it didn’t always reflect across systems instantly, which impacted table planning and service flow. On peak nights, even small discrepancies could create ripple effects for the team on the floor.
Staffing pressure compounded the issue. Labour is one of the biggest costs for any venue, and in a space like The Bootlegger, where Fridays and Saturdays can look very different to a jazz Sunday or a cocktail masterclass, forecasting accurately is critical.
“When you’re juggling live music, the rooftop, functions and regular dining all at once, you need a clear view of what’s coming up. If your booking data isn’t clean or centralised, it’s hard to roster confidently.”
On top of that, The Bootlegger regularly hosts functions and special events, from cocktail masterclasses to private celebrations. These come with packages, minimum spends, prepayments and specific space allocations, including the Secret Garden Rooftop. One missed note or overlooked detail can derail an otherwise perfectly planned night.
“There’s a lot more complexity behind the scenes than people realise; one missed dietary note or an incorrect guest count can impact the whole flow of the evening,”
Great service starts behind the scenes
Since switching to Now Book It, The Bootlegger has brought bookings, guest details and event visibility into one centralised platform. This immediately meant less manual admin and more clarity.
“Our online reservations have been much smoother and more consistent. Guests find it easy to use on mobile, bookings come through cleanly, and it’s reduced the back-and-forth for the team, especially during peak periods.”
Instead of juggling emails, DMs and separate booking tools, the team now has one clear source of truth. Guest details, booking notes, dietary requirements and changes are stored together. If a time shifts or numbers change, the update is reflected in real time. That centralisation has significantly reduced missed messages and double handling. During busy service, that translates directly to time saved and fewer service disruptions.
“We’ve loved having everything in one place, you’re not digging through emails or checking multiple inboxes. It’s all there, guest details, notes, changes. It sounds simple, but it’s made a big difference,”
The visibility into upcoming bookings has also sharpened forecasting. With a clearer picture of covers and capacity, the team can plan staffing and prep with more confidence. Rather than reacting to surprises, they’re working from reliable data.
“It’s helped us protect service standards on busy nights, we can see what’s coming up and roster accordingly. That confidence changes the way you approach a weekend.”
From a revenue perspective, making it easier for guests to book, particularly on mobile, has driven more consistent online reservations. Instead of losing potential diners to unanswered calls or slow email replies, guests can lock in their table instantly.
“Overall, it’s had a positive impact on bookings and revenue. When it’s easy for guests to secure a table, you naturally convert more interest into confirmed reservations,” said Kelly.
Managing music, meals, and masterclasses
The Bootlegger doesn’t just rely on standard dining bookings. Their events calendar is a core part of their identity, from live music to themed nights and hands-on experiences like their Bootlegger Cocktail Masterclasses. Using Now Book It’s events feature, the team can set up special events with full prepayment required at the time of booking. This not only secures revenue upfront but also significantly reduces no-shows and last-minute cancellations.
Instead of manually chasing payments or reconciling transfers, everything is handled at the point of booking. Guests secure their spot, the payment is processed, and the team has a clear attendee list in one place. That streamlined workflow frees up time and reduces risk. For events that involve allocated seating, curated drinks and specific stock ordering, certainty around numbers is crucial.
“It’s made event planning smoother, we know exactly who’s coming, what they’ve paid and what we need to prepare. There’s no ambiguity.”
Scaling without sacrificing the guest experience
At its core, The Bootlegger’s success comes down to experience. Whether guests are there for a whiskey flight, a rooftop cocktail, a BBQ feast or a Sunday jazz session, the promise is the same – you’re in for a huge night out.
But delivering that consistently at scale requires operational discipline. By consolidating bookings, improving visibility and reducing manual admin, Now Book It has allowed Kelly and her team to focus more on hospitality and less on chasing details. The Bootlegger isn’t standing still. Their entertainment calendar continues to evolve, their drinks list keeps expanding, and their rooftop remains one of Katoomba’s worst-kept secrets. With a booking system that supports their ambition rather than slowing it down, they’re well placed to keep growing.
“When your systems work with you instead of against you, it changes everything, It gives you the space to think bigger,” Said Kelly.
For venues balancing food, drinks, entertainment and events under one roof, The Bootlegger’s story is proof that the right booking platform isn’t just about filling tables, it’s about protecting the experience that keeps guests coming back.
Book a table at The Bootlegger Bar
Now Book It tip: Book for a little earlier and start your night with a whiskey flight from their signature “Liquid Smoke” cocktail, then share one of the Low & Slow BBQ platters – we promise it won’t disappoint.