What's On at Cupitt's Estate

DECEMBER - 25 & 26

JANUARY 26

FEBRUARY - 20th, 27th - (Private Events - Cellar Door open till 1pm)

MARCH - 5th, 13th, 30th, 26th - (Private Events - Cellar Door open till 1pm)

All the Fuss are back this Sunday, 21 December, 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!

We're bringing the good times with local favourites The Castaways live from 12:30pm. Whether you’re looking to chill in our cool, air-conditioned restaurant with a delicious lunch or soak up the summer vibes on the hill, we have the perfect spot for you.

All the Fuss are back this New Years Day, with their signature mix of neo soul, funk and blues grooves.

Think smooth vocals, sax, bass and plenty of energy, All The Fuss always bring the vibe and get the crowd moving.

Grab a glass, settle in, and let’s make it a New Years Day to remember!

Bookings are recommended.

A good wine deserves a good soundtrack.

Our very own, Tommy Disco (aka Tom Cupitt) is on the decks from 5pm - serving up soul, funk and breezy feel-good grooves to match the view.

Bring your friends, tuck into a pizza and celebrate the weekend with a glass of Cupitt’s wine.

It’s laid-back, a little retro, and exactly what Fridays should feel like.

Bookings recommended.

Catch The Stayers Live at Cupitt's Estate – Sunday, 4th January!

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, bluesy grooves, The Stayers deliver music that hits the heart and moves the soul.

Come for the music, stay for the vibes. We can’t wait to see you!

Add a little fun to the start of your weekend with our Friday Sunset Session.

Tall Shaun will be entertaining you this week with their truly unique and authentic musical style that breathes fresh life into contemporary and alternative melodies.

Gather your friends, order one of our pizzas and some bites to share and cheers to the weekend over a glass of Cupitts wine.

Bookings recommended.

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. It’s the perfect way to reset after the festive madness, so round up the crew and enjoy great music, delicious food and fabulous NSW wine.

Charlie & Sarah are a folk duo blending the dreamy, nature-soaked songwriting of Sarah Fallon with the playful, old-soul troubadour spirit of Charlie Lane. Together, Charlie & Sarah create gentle, harmony-rich performances that feel both nostalgic and new.

Gather your friends and join us for delicious food, great wine, and a night filled with smooth tunes.

Join us on Sunday, January 18th for an unforgettable afternoon of live music from the Jackee B Trio. With a fusion of cool rock, folk and alternative country, the Jackee B Trio will captivate you with rich guitar arrangements and evocative storytelling.

Settle in with refreshing cocktail specials, some light eats and soak up the good vibes!

Add a little fun to the start of your weekend with our Friday Sunset Session.

Enjoy a good laugh and a toe-tap as Dave Newman entertains you with his engaging character and classic acoustic hits.

Gather your friends, order one of our pizzas and some bites to share and cheers to the weekend over a glass of Cupitts wine.

Bookings recommended.

Settle in for a perfect Sunday lunch among the vines as we welcome this vibrant 7-piece band to the winery.

Blending classic and contemporary funk, soul, and disco favourites, they’ll bring smooth grooves, sunny rhythms, and feel-good energy to your afternoon. 

With rich horn lines and soulful vocals floating through the open air, it’s the ideal soundtrack for great wine, good company, and a laid-back day outdoors.

We’re excited to welcome Solo West to Cupitt's Estate!

This talented South Coast multi-instrumentalist brings an upbeat mix of your favourite covers from the ’70s through to today. Whether you’re singing along, tapping your feet, or simply soaking up the good vibes, Solo West always brings the fun.

Gather your friends and join us for delicious food, great wine, and a night filled with music and merriment!

Bookings recommended

Join us on Sunday, February 1st for an unforgettable afternoon of live music from Horse Drawn Cadillac—bringing the heat with everything from gritty Chicago blues to Mississippi stomps, swampy country blues, and a hit of Southern funk.

Settle in with refreshing cocktail specials and soak up the good vibes as we roll into the season in style. It’s going to be a full-tilt boogie, and trust us—you won’t want to miss it!

Catch The Stayers Live at Cupitt's Estate – Sunday, 15th January!

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, bluesy grooves, The Stayers deliver music that hits the heart and moves the soul.

Come for the music, stay for the vibes. We can’t wait to see you!

Add a little fun to your Sunday afternoon with our Sunday Session featuring Dave Newman.

Settle in for a relaxed and uplifting end to the week as Dave brings his engaging charm and classic acoustic hits to the Wine Garden. Expect plenty of laughs, toe-tapping tunes, and the perfect laid-back Sunday vibe.

Gather your friends, grab one of our wood-fired pizzas and some bites to share, and enjoy a glass of Cupitt’s wine as you unwind into the evening.