What's On at Cupitt's Estate

Live music & special events every week

Dates we are not open to the public

AUGUST - 14th, 28th

NOVEMBER - 6th, 17th

Cellar door is open from 9am until 1pm for sales and 11am to 12:30pm for tastings

Cupitts Estate Entertainment Cupitts Estate Entertainment

Magic Dan I From 3:30pm

Family Fridays I May 30

Join us this Friday for Family Friday - the perfect way to relax and reconnect at the end of the week.

Kids will be entertained by the fabulous Magic Dan - loads of fun with balloons, games, magic tricks and face painting!

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Dinner at Cupitt's Estate Dinner at Cupitt's Estate

May 29th I from 5:45pm

Pasta e Vino

Join us for a midweek Italian escape with Pasta e Vino nights at Cupitt's Estate.

Enjoy a rotating two-course menu featuring delicious handmade pasta and seasonal entrée – all for $55. Want to make it extra special? Add two perfectly matched glasses of estate wine for just $20.

It's relaxed, hearty, and the perfect way to wind down your week.

Bookings recommended. Walk-ins welcome.

Keith Zehr | June 1st

Sunday Session | 12:30PM

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!

Simon Marnie smiling Simon Marnie smiling

Intimate Long Lunch | 12pm

Conversations with Simon Marnie I June 6th

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)

Music at Cupitts Estate Music at Cupitts Estate

Harmony Music I From 3:30pm

Family Fridays I June 6th

Join us this Family Friday for a heartwarming evening as Harmony Music graces us with her beautiful voice and soulful sound. It’s the perfect way to bring the family together and ease into the weekend.

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Fun activities will entertain the kids each week, leaving you free to unwind and enjoy. Book your table and make Friday night a family tradition at Cupitt's Estate.

Minnie & The Moonrakers | June 8th

Sunday Session | 12:30PM

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.

Entertainment for Families at Cupitts Entertainment for Families at Cupitts

Magic Dan I From 3:30pm

Family Fridays I June 13

Join us this Friday for Family Friday - the perfect way to relax and reconnect at the end of the week.

Kids will be entertained by the fabulous Magic Dan - loads of fun with balloons, games, magic tricks and face painting!

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Horse Drawn Cadillac | June 15th

Sunday Session | 12:30pm

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.

June 21

Storyfest Feature I Dinner

SOLD OUT

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.

All the Fuss | June 22nd

Sunday Session | 12:30PM

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!

Music at Cupitts Estate Music at Cupitts Estate

Harmony Music I From 3:30pm

Family Fridays I July 4th

Join us this Family Friday for a heartwarming evening as Harmony Music graces us with her beautiful voice and soulful sound. It’s the perfect way to bring the family together and ease into the weekend.

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Fun activities will entertain the kids each week, leaving you free to unwind and enjoy. Book your table and make Friday night a family tradition at Cupitt's Estate.

Richard & The Lionhearts | July 6th

Sunday Session | 12:30PM

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!

Cupitts Entertainment for Families Cupitts Entertainment for Families

Magic Dan I From 3:30pm

Family Fridays I July 11

Join us this Friday for Family Friday - the perfect way to relax and reconnect at the end of the week.

Kids will be entertained by the fabulous Magic Dan - loads of fun with balloons, games, magic tricks and face painting!

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

The Castaways | July 20th

Sunday Session | 12:30PM

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.

Sunday Lemonade Solo | July 27th

Sunday Session | 12:30pm

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.

Music at Cupitts Estate Music at Cupitts Estate

Harmony Music I From 3:30pm

Family Fridays I August 1st

Join us this Family Friday for a heartwarming evening as Harmony Music graces us with her beautiful voice and soulful sound. It’s the perfect way to bring the family together and ease into the weekend.

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Fun activities will entertain the kids each week, leaving you free to unwind and enjoy. Book your table and make Friday night a family tradition at Cupitt's Estate.

Entertain and Feed your Family at Cupitts Entertain and Feed your Family at Cupitts

Magic Dan I From 3:30pm

Family Fridays I August 8th

Join us this Friday for Family Friday - the perfect way to relax and reconnect at the end of the week.

Kids will be entertained by the fabulous Magic Dan - loads of fun with balloons, games, magic tricks and face painting!

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Music at Cupitt's Estate Music at Cupitt's Estate

The Stayers I August 10th

Sunday Session I 12:30pm

Catch The Stayers Live at Cupitt's Estate – Sunday, 10th August!

Join us for an unforgettable afternoon of delicious eats, exceptional wine, and the feel-good, stripped-back sound of The Stayers. Known for their well-crafted songs and cool grooves, The Stayers deliver music that hits the heart and moves the soul.

Don’t miss out – it’s the perfect way to wind down your weekend.

Music at Cupitt's Estate Music at Cupitt's Estate

Dave Newman I August 17th

Sunday Session I 12:30pm

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!

All The Fuss I August 31st

Sunday Session I 12:30pm

Turn up the heat this winter with the soulful sounds ofAll the Fuss! Their irresistible mix of funk and feel-good vibes will have you dancing your way through the afternoon. Add in mouth-watering food, flowing wine, and stunning vineyard views—and you’ve got the ultimate winter escape. Gather your crew and book your table now for an afternoon you won’t want to miss!

Music at Cupitts Estate Music at Cupitts Estate

Harmony Music I From 3:30pm

Family Fridays I September 5th

Join us this Family Friday for a heartwarming evening as Harmony Music graces us with her beautiful voice and soulful sound. It’s the perfect way to bring the family together and ease into the weekend.

Enjoy our $75 Family Meal, which includes two delicious pizzas, a fresh salad, a jug of soft drink, and your choice of two glasses of house wine or beer.

Fun activities will entertain the kids each week, leaving you free to unwind and enjoy. Book your table and make Friday night a family tradition at Cupitt's Estate.

Sunday Session I 12:30pm

All The Fuss I September 28th

The Fuss are back this Sunday, 28 September, bringing their infectious beats and feel-good vibes. Expect an afternoon filled with music that’ll have you tapping your toes and moving to the rhythm. Round up your friends, grab a table, and soak up the sun while enjoying a delicious lunch!

All The Fuss I October 26

Sunday Session I 12:30pm

This Sunday, October 26th , All The Fuss are back to light up your afternoon with their infectious rhythms and soulful tunes. Their dynamic setlist promises to keep you dancing all day long. Gather your friends, reserve a table, and indulge in a delectable lunch while soaking up the sunshine. It's the perfect way to spend your Sunday!

All The Fuss I December 21st

Sunday Session I 12:30pm

All The Fuss are back on Sunday, December 21st, with their fantastic toe-tapping jams guaranteed to get you grooving all afternoon. Gather your friends, book a table, and enjoy a delicious lunch in the sunshine.