What's On at Cupitt's Estate

From 3 September, we’re opening the Dining Room every Thursday night for Rosie’s French Table. It is a new menu inspired by Rosie Cupitt’s love of France, created together with Executive Chef Ryan Smith.

Rosie’s French Tableis designed to be an easy midweek dinner as much as it is an excuse to make a night of it.

Two courses | $59 per person

Three courses | $75 per person

*Special menu item is subject to change.

Dine with us mid-week this August and enjoy our lunch special.

Confit duck leg with a white bean and chorizo cassoulet for $29

Add your first glass of Nebbiolo wine for $10

Lunch Mon - Fri - either in the Dining Room or Wine Garden

*Special menu item is subject to change.

As the sun sets and the fire pits are lit, settle in for a relaxed evening in the Wine Garden.

Fire + Smoke Night brings together slow-cooked meats, Cupitt's wines and live music from Tall Shaun where we celebrate the best of the South Coast.

Pre-order your meat pack -Our delicious slow-cooked meat packs are available by pre-order, with very limited numbers available on the day. We recommend reserving yours when you make your booking. Packs are ordered per person.

> BBQ Beef Short Ribs Pack(serves 1) - Includes House Slaw, Charred corn salsa plus pickles, sauce and bread. $39

> Pork Shoulder Pack(serves 1) - Includes House Slaw, Roasted potato, sour cream and chives plus pickles, sauce and bread. $39

Our full Casual Menu will also be available until 7pm for guests who prefer other options.

Tall Shaun’s original blues and alt-country sound brings a soulful, easy rhythm to the evening, carrying you from sunset and well into the night.

Kid's face painting will also be available to keep the kids entertained.

Come settle in, take in the views, and ease into the weekend the Cupitt’s way.

This Father’s Day, show your appreciation for the superheroes in our lives and treat him to a memorable day out at Cupitt's Estate.

Enjoy the soulful sounds of Soul Tonic as they bring their signature blend of smooth grooves, heartfelt classics and feel-good favourites to the stage. Whether performing beloved hits or putting their own spin on timeless tracks, Soul Tonic create the perfect laid-back vibe — guaranteed to have you smiling, swaying and soaking up the moment.

Make the day extra special by booking into the Cupitt’s Estate Restaurant for a beautiful 3-course menu, thoughtfully curated for the occasion. Or reserve a table in the Wine Garden and gather the whole family for a relaxed celebration filled with great music, delicious food and award-winning wines.

Bookings recommended.

A Night of Wine, Cheese + Stargazing | 1 hour

Embark on a captivating space journey, vino in hand. Experience this one-of-a-kind stargazing night. Indulge yourself with wine and cheese on arrival under the stars, a stargazing session led by an astronomer and exploration of the Southern Sky - planets, galaxies, stars, constellations and galaxies through the telescope.

This pairs perfectly with cozy dinner at 7.45pm in the Dining Room.

Beloved locals Richard & The Lionhearts are here to remind us why we love live music so much! With their feel-good tunes and a knack for getting a crowd moving, they’ll have your toes tapping, your hips swaying (no judgment), and your spirits soaring.

Spend your Sunday soaking up live music at Cupitt’s with the Jackee B Trio. Set against the stunning backdrop of our vineyard, Burrill Lake, and the Budawang Mountains, enjoy a relaxed afternoon of smooth vocals, acoustic guitar, and rich harmonies.

The trio will perform a mix of laid-back covers, providing the perfect soundtrack to your long lunch or afternoon drinks.

Live Music Sundays are a South Coast favourite- come see why!

Join us on Sunday 27th September as All The Fuss return to the winery for another unforgettable afternoon of live music, great wine, and good vibes. With their signature toe-tapping tunes and crowd-favourite jams, they’ll have you grooving the afternoon away. Round up your friends, book a table, and enjoy a delicious lunch in the sunshine while soaking up the sounds of a perfect Sunday session.

A Night of Wine, Cheese + Stargazing | 1 hour

Embark on a captivating space journey, vino in hand. Experience this one-of-a-kind stargazing night. Indulge yourself with wine and cheese on arrival under the stars, a stargazing session led by an astronomer and exploration of the Southern Sky - planets, galaxies, stars, constellations and galaxies through the telescope.

This pairs perfectly with an early dinner at 5.45pm in the Dining Room.

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.

Join Avril and special guest Wendy McCarthy AC for an honest and inspiring conversation about leadership, equality and a life remade more than once.

“I was called difficult, disruptive, too direct, too political, too much. I was also trusted, sought out, and invited into rooms where decisions were made.”Born in apartheid South Africa and raised to stay in line, Avril Henry spent her life crossing it.

Wendy McCarthy AC is a respected leader, author, and lifelong advocate for gender equality, education, and social reform, shaping policy & culture across health, business, media, and the arts. She helped establish the Women’s Electoral Lobby, has been Deputy Chair of the ABC, Chair of headspace, and Chancellor of the University of Canberra. In 2024, she was awarded the NSW Excellence in Women’s Leadership, and in 2025 the Trailblazer Award from Future Women. She is a Companion of the Order of Australia and the author of Don’t Be Too Polite Girls.

Your ticket includes sparkling on arrival, canapés and a two-course meal. $95

Signed hard-cover copies of Avril’s book ‘Not All Diamonds Are Worn’ will be available for purchase on the night.

Tickets are limited, we expect this one to sell out

Hitch a ride in the Cadillac and join us for a Sunday Session at Cupitt's Estate.

We have Horse Drawn Cadillac bringing their infectious energy to the stage. Think Chicago blues, vibrant brass, harmonica, big vocals and a whole lot of grooving. 

One not to be missed. We'll see you there!

Spend your Sunday afternoon with The Castaways, an acoustic duo serving up a laid-back mix of pop, folk, country, and blues favourites. Their groovy, feel-good tunes are the perfect soundtrack to a summer afternoon in the Wine Garden.

Settle in with a leisurely lunch, your favourite glass of wine, and good company while enjoying live music surrounded by vineyard views.

Get ready for a Sunday Session at the winery as Horse Drawn Cadillac return on December 20th! 

With their high energy, infectious stage presence, they’ll have you grooving the afternoon away. 

Gather your friends, book a table, and settle in for a delicious lunch, great wine, and sunshine-filled afternoon.