What's On at Cupitt's Estate

MAY - 2nd, 8th

AUGUST - 14th, 28th

NOVEMBER - 6th, 17th

Cellar door is open from 9am for sales and 11am to 12:30pm for tastings

Join us for a Sunday of well-known tunes from the 60s through to the 90's & beyond! Rock, folk, country & blues! The Freewheelers duo will liven up your Sunday afternoon with a dynamic set to suit all ages.

Savour one of our much-loved pizzas, soak up the stunning sunset over the mountains, and relax as the weekend draws to a close.

Booking is recommendedto secure your spot!

Kick off your weekend with the captivating sounds ofAmy & I. This talented duo, featuring Simon Kinch and Amy Smith, blends acoustic folk, heartfelt harmonies, and a mix of favourites and originals for a truly mesmerising performance. With guitar, keys and seamless synchronicity, their music creates the perfect atmosphere for a relaxed Friday evening. Enjoy a delicious dinner, a glass of wine, and let the music ease you into the weekend.

Through their endless support and unconditional love, Mum's do it all! Show your admiration for the true superheroes of our world, and treat her to a wonderful day out at Cupitt's Estate.

Join us for an unforgettable afternoon with live music from Soul Tonic! Sunday from 12:30 to 3:30PM, spoil Mum with good vibes, great food, wine and beer, and fantastic company.

Book your table early to ensure you don't miss out. We can't wait to celebrate with you!

This event is an intimate, hands-on experience designed for food and wine lovers who appreciate artisanal craftsmanship. Guests will learn the principles of pairing wine with cheese while also getting insider tips on how to make cheese at home.

Ease into Sunday with The Castaways, an acoustic duo bringing a mix of pop, folk, country, and blues classics to the Wine Garden. Their warm, stripped-back sound sets the perfect tone for a relaxed afternoon. Sit back with a long lunch, a glass of wine, and great company as you soak up the music and the scenery.

Rooted in the Italian way of life—simple pleasures, shared tables, long conversations, and generous hearts. The event is a love letter to la dolce vita—the sweet life. Each participating producer shares not just food or drink, but a story tied to an Italian value or saying.

Join us for this collaborative dinner featuring the masters of South Coast hospitality, including Cupitt's Winemaker Wally, Ian from Martin Ridge, Jon from Lagom Bakery, Jesse of Duro Pasta, Kitty, and Nat from Milkhaus.

Tickets: $85 per person (including a donation to Shoalhaven Food Network)

Bring your Sunday to life with the smooth neo-soul, funk, and RnB grooves of All the Fuss. Their rich, rhythmic sound sets the perfect backdrop for a relaxed afternoon in the Wine Garden. Sip on a crisp glass of wine, indulge in a delicious lunch, and let the music carry you through the day. The ultimate Sunday unwind awaits.

Keith is an amazing Sydney soloist, and with his massive song list can appeal to all ages and covers all styles of music from rock to ballads. Keith's mesmerizing voice and ability to captivate audiences will make this Sunday Session unmissable. Book your table now to join the fun!

Conversations with Simon Marnie - An intimate long lunch at Cupitt’s Estate

Join us for a very special afternoon of conversation, great food, and shared stories with one of Australia’s most beloved broadcasters—Simon Marnie.

For over 20 years, Simon was the familiar weekend voice of ABC Radio Sydney, hosting the iconic Weekend Mornings program. From championing local producers and uncovering regional gems to sharing his love of music, food, and community connection, Simon's storytelling shaped the rhythm of Saturdays and Sundays across NSW.

In late 2024, Simon’s departure from the ABC came as a shock to many, prompting an outpouring of affection from his loyal listeners and the hospitality community he’s long supported. This event is a chance to honour his contribution, hear his reflections, and toast to what’s next—with a long lunch shared in true Simon style: generously, joyfully, and with heart.

The experience includes: 

A welcome drink on arrival 

Three-course shared feast featuring seasonal produce

A fireside-style conversation hosted by Rosie Cupitt 

Q&A with Simon

Come ready for a relaxed afternoon filled with warmth, connection, and stories from a broadcaster who’s truly left a mark on the Australian media landscape.

Limited tickets are available.

Tickets - $95 (includes a $5 donation to Shoalhaven Food Network)

Groove your Sunday afternoon away with Minnie & The Moonrakers. Enjoy a lively, toe -tapping hybrid of fifties rock n' roll fused with swampy blues, swing and rockabilly from 12.30PM to 3:30PM.

Book your table in the Wine Garden for the full experience to finish off your Sunday and catch the tunes. We can't wait to see you there.

Spend your Sunday afternoon soaking up live music in the Wine Garden.

From 12:30 to 3:30 pm, Horse Drawn Cadillac will bring their rich, soulful sound to the stage, setting the scene for a perfect day out. Settle in with a long lunch, a glass of your favourite wine, and great company as the music carries you through a relaxing afternoon.

Make the most of your Sunday with us.

Stephanie Alexander AO is regarded as one of the greats of Australia’s food industry, a reputation earned through her thirty years as owner-chef of several restaurants, as the author of 20 influential books and hundreds of articles about food, and for her groundbreaking work in creating the Stephanie Alexander Kitchen Garden Foundation. Stephanie’s fifth book, The Cook’s Companion is an Australian classic and has sold more than 500,000 copies.

Join Stephanie and journalist Joanna Savill for an intimate evening of great stories and delicious food prepared in partnership with staff at Cupitt’s Estate as we head towards the 30th anniversary release of The Cook’s Companion in early 2026.

Warm up your winter with the grooves of All the Fuss. Their unique blend of funk and soul will brighten any chilly afternoon. Add great food and flowing wine, and you’ve got the perfect winter escape. Book your table now to join the fun!

Delight in the smooth sounds of Richard & The Lionhearts, set against the stunning backdrop of our vineyard, Burrill Lake, and the Budawang Mountains. From 12.30pm to 3.30pm, unwind on our lush estate grounds as talented musicians take the outdoor stage, offering the perfect soundtrack to your leisurely Sunday.

Secure your table now and make it a day to remember!

Ease into Sunday with the soulful sounds ofThe Castaways—an acoustic duo bringing feel-good vibes to the Wine Garden. From smooth folk to classic blues and toe-tapping pop, their music is the perfect soundtrack to a lazy afternoon. Join us from 12:30 to 3:30, gather your crew, settle in with a glass of wine, and let the good times roll in a setting made for relaxing.

Join us for an afternoon of cruisy vibes and soulful tunes asSunday Lemonadetakes the stage for their Solo Sunday Session. With a mix of indie folk and roots, they'll have you tapping your toes and swaying along in no time.

Sit back, relax with a glass of your favourite wine, and enjoy a long lunch as the music sets the perfect tone for a laid-back afternoon in great company.

Join us for a Sunday of Toe-Tapping Tunes with Dave Newman!

Finish off your weekend with an unforgettable afternoon of live music as Dave Newman performs his signature blend of classic acoustic hits.

Enjoy one of our famous pizzas, take in the breathtaking sunset over the mountains, and unwind as the weekend comes to a close.

Booking is recommendedto secure your spot!