Heritage in a Glass: Libby Cupitt on the Story Behind Cupitt’s Estate
Perched between the rolling hills of the South Coast hinterland and the glistening shores of Mollymook, Cupitt’s Estate is more than just a winery—it’s a vibrant celebration of family, craftsmanship, and the joy of good food and wine shared. We sat down with Libby Cupitt, Strategic Partnerships Manager and second-generation steward of the family-run estate, to chat about Cupitt’s evolution, the magic of their wedding offerings, and the beating heart behind one of NSW’s most beloved hospitality experiences.
A Legacy Rooted in Passion
Libby, can you tell us about the origins of Cupitt’s Estate? How did it all begin?
The story of Cupitt’s Estate is one deeply entwined with our family’s love for the land, wine, and each other. It all began when my in-laws, Rosie and Griff Cupitt, made the move from Bowral to the South Coast in search of a slower, more grounded lifestyle. Griff took up farming Black Angus cattle on a property in Ulladulla, but it was Rosie who saw a grander vision—after falling in love with winemaking on trips through France, she imagined a vineyard, winery, and hospitality experience that brought a slice of that European charm to the Milton-Ulladulla region.
What started with grapes quickly expanded into so much more. A boutique winery became a restaurant, then a wedding venue, and now also a series of luxury villas. And through it all, the foundation has remained the same: good wine, good food, and heartfelt hospitality. For the past 12 years, the second generation, my husband Tom, his brother Wally, and myself, have taken the reins, working closely with Rosie and Griff to grow the dream.
The Heart of the Estate
Cupitt’s has evolved so much—what values have stayed the same over time?
Even as we’ve expanded into new offerings and experiences, the soul of Cupitt’s remains unchanged. We’re still deeply guided by family values, sustainability, and craftsmanship. We’ve always believed in creating something honest—something that reflects who we are and where we live.
We may be winemakers, but first and foremost, we’re hosts. Every person who visits the estate is treated like an old friend, welcomed into our home to enjoy something we’ve poured love and care into creating. That philosophy touches everything—from the warmth of our team to the way we design our menus.
A Destination Beyond the Glass
What makes Cupitt’s Estate stand out from other South Coast wineries?
There’s definitely something special about our spot. We’re nestled in this beautiful rural setting just minutes from the beach,so whether you’re here for wine tasting, a long lunch, a weekend escape, or a wedding, there’s a full experience waiting for you.
What truly sets us apart, though, is our breadth. We’re the only winery in the region with boutique on-site accommodation—ten villas and a four-bedroom, pet-friendly house. We’ve built a place where you can really settle in, enjoy live music, explore our food and drinks, and take in the views. And we’re here 7 days a week, with a team of over 100 people passionate about what they do.
The Cupitt Experience
How does your family’s love for wine, food, and hospitality shape the guest experience?
Rosie’s passion for hospitality is legendary, she’s the type of person who makes you feel instantly at ease, and that spirit flows through everything we do at Cupitt’s. We want guests to feel relaxed, inspired, and connected. Our wine tells a story of the land and the hands that made it. Our food, crafted from seasonal and local ingredients, elevates that story.
We design our menus to complement our wine, not the other way around. There’s constant collaboration between our chefs and winemakers,lots of (very serious!) tasting sessions, where we all sit down and experience how the flavours interact. It’s all about creating a journey for the senses.
Wine, Food, and Sustainability
Tell us about your winemaking philosophy and what makes Cupitt’s wines distinct.
Our approach is grounded in minimal intervention, letting the fruit shine and tell its story. We take cues from traditional European methods, particularly Italian winemaking, which pairs beautifully with our coastal lifestyle and climate.
We’re especially passionate about varietals like Vermentino, Fiano, Nebbiolo, and Montepulciano. They require less water, thrive in Australian conditions, and bring something new to the glass. We source fruit from select growers across Southern NSW—regions like Hilltops, Tumbarumba, and the Canberra District—all full of exciting potential.
And for those curious, our Rosé is an undeniable crowd favourite, with easy going charm and South Coast vibes. Our award-winning Chardonnay is also a must-try, and our cellar door team is always happy to guide visitors through a tailored tasting experience.
How do you approach sustainability?
For us, sustainability isn’t a checkbox,it’s a mindset. Whether it’s choosing climate-appropriate grape varietals, composting grape marc to enrich our vineyard soil, or reducing kitchen waste, we’re always striving for balance.
But sustainability is also about people. We’re committed to being a great place to work, to supporting our local community, and to building a future where Cupitt’s can continue to thrive for generations to come.
Weddings with Heart
Cupitt’s is a dream wedding location—what makes it so magical?
I may be a little biased-my husband Tom and I were married here in 2011! But truly, it’s the combination of natural beauty, incredible food and wine, and the warmth of our team that makes it unforgettable. Couples and guests alike tell us it feels like coming home.
We offer everything in one place: a picturesque vineyard setting, luxury accommodation, a winery, award-winning cuisine, and plenty of opportunities for connection.From pre-wedding dinners to post-wedding recovery parties. Whether you’re eloping with just a handful of guests or planning a big celebration, we tailor the experience to each couple.
Any standout weddings that come to mind?
There have been so many beautiful, personal moments, but one of the most memorable was hosting Matty J and Laura Byrne’s wedding (yes,from The Bachelor). They wanted somewhere relaxed, dog-friendly (of course Buster was part of the day!), and effortlessly elegant. It was a joy to help bring their vision to life.
What we love most is when couples add their own flair—picnic-style receptions, custom cocktails, live music under the stars. Every celebration at Cupitt’s becomes part of our story too.
Finally, what do you hope guests take away from their time at Cupitt’s Estate?
I hope they leave feeling nourished,in every sense. Nourished by the food, the wine, the views, the people. Whether they’re celebrating a milestone or just dropping in for lunch, we want them to feel the magic of this place we call home.
To explore more of Cupitt’s Estate or plan your next visit, head to cupittsestate.com.au.
