What's On at Cupitt's Estate
Live music & special events every week

There’s always something happening at our place! From weekly live music sessions and seasonal events to updates on special experiences and days we're closed, this is the best spot to keep up with what’s going on. Whether you're planning a relaxed visit with friends or looking to join one of our signature events, you’ll find all the details you need right here. Check back regularly so you don’t miss a beat!
Mid-week in August
Local's Lunch
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.
Family Meal Deal | 5pm
Family Friday | 21st August
Join us this Friday from 5pm for a cosy family night out!
We’ll have fire pits, marshmallows, a bubble machine and lawn games for the kids to enjoy.
Pair it with our specialFamily Meal + Drink Deal for just $75:
Kids’ pizza
Pizza of your choice
Fresh salad
Jug of soft drink
Your choice of two glasses of house wine or beer
This is ourfinal Family Friday for Winter 2026, but don’t worry — we’ll still be serving our casual menu on Friday nights, with kids always welcome!
Bring the family, settle in and make a night of it.
Sunday Session | 12:30pm
Horse Drawn Cadillac | 23rd August
Join us on Sunday for a great afternoon of live music from Horse Drawn Cadillac. They bring everything from gritty Chicago blues to Mississippi stomps, swampy country blues, and a hit of Southern funk. It's a lot of fun.
Grab your friends, relax on the lawn, and let the music, wine, and views make this a Sunday to remember.
with Tall Shaun | from 5pm
Fire + Smoke Night | 4th September
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.
Sunday Session | 12:30pm
Fathers Day with Soul Tonic | 6th September
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.
Stargazing | 6.30pm
Sip Under the Stars | 12th September
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.
Sunday Session | 12:30pm
Richard and the Lionhearts | 13 September
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.
Sunday Session | 12:30pm
Jackee B Trio | 20th September
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!
Sunday Session | 12:30pm
All The Fuss | 27th September
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.
Stargazing | 7.30pm
Sip Under the Stars | 10th October
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.
Sunday Session | 12:30pm
The Castaways | 11th October
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.
Sunday Session | 12:30pm
Horse Drawn Cadillac | 1st November
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!
Sunday Session | 12:30pm
The Castaways | 6th December
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.
Sunday Session | 12:30pm
Horse Drawn Cadillac | 20th December
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.
