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)

Ease into the weekend with our Friday special. Enjoy a $10 glass of Prosecco when you order the weekly small plate. This week we have Vanella burrata with house focaccia and a bright chardonnay fennel jam.

With entertainment from DJ Tommy Disco, dance the evening away with family and friends.

Delight in the bluesy sounds of The Stayers, 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.

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

Join us for our Christmas Catch Up at Cupitts, a relaxed sunset session made for families, friends, and anyone who loves a bit of silly season fun. Harmony Music will be singing your favourite Christmas songs as the sun drops behind the hills, setting the tone for an easy, joy filled evening.

We’ll have a photo booth ready for your family Christmas snaps, a little station for the kids to write their letters to Santa, fun lawn games, and a fresh Christmas sangria for the grown ups. It’s the kind of night where everyone feels welcome, the kids can run free, and you can unwind with a glass in hand.

Two dates only, 12 and 19 December. Bring the crew and settle in for a gentle South Coast sunset, good food, and a bit of festive cheer.

Ease into the weekend with our Friday special. Enjoy a $10 glass of Prosecco when you order the weekly small plate. This week we have Vanella burrata with house focaccia and a bright chardonnay fennel jam. A relaxed way to finish the week with friends and a good glass in hand.

Join us on Sunday, December 14th for an unforgettable afternoon of live music from The Specialties. With a unique spin on classic Blues, Jazz, Rockabilly, and Soul, the band features some of Sydney’s finest musicians.

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!

Join us for our Christmas Catch Up at Cupitts, a relaxed sunset session made for families, friends, and anyone who loves a bit of silly season fun. Harmony Music will be singing your favourite Christmas songs as the sun drops behind the hills, setting the tone for an easy, joy filled evening.

We’ll have a photo booth ready for your family Christmas snaps, a little station for the kids to write their letters to Santa, fun lawn games, and a fresh Christmas sangria for the grown ups. It’s the kind of night where everyone feels welcome, the kids can run free, and you can unwind with a glass in hand.

Two dates only, 12 and 19 December. Bring the crew and settle in for a gentle South Coast sunset, good food, and a bit of festive cheer.

Ease into the weekend with our Friday special. Enjoy a $10 glass of Prosecco when you order the weekly small plate. This week we have Vanella burrata with house focaccia and a bright chardonnay fennel jam. A relaxed way to finish the week with friends and a good glass in hand.

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.

Come and join us for live music with our Friday Sunset Sessions every weekend during the Summer holidays.

It's the perfect reason to gather your mates and watch the sun go down with a glass in your hand.

Stay tuned for more details!

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.

Come and join us for live music with our Friday Sunset Sessions every weekend during the Summer holidays.

It's the perfect reason to gather your mates and watch the sun go down with a glass in your hand.

Stay tuned for more details!

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.

Come and join us for live music with our Sunday Sessions every weekend during the Summer holidays.

It's the perfect reason to gather your mates for an afternoon of good food, great music and Cupitts delicious wines and cocktails.

Stay tuned for more details!

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!