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. A relaxed way to finish the week with friends and a good glass in hand.

Join us on Sunday, November 30th 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!

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.

Welcome the festive season with a creative afternoon at Cupitt’s Estate. Guided by our own talented Martha and guest floristry artist Clare Lewis-Evans (formerly of Gypsy Carmen), this hands-on workshop invites you to design and craft a beautiful, bespoke Christmas wreath to take home.

Whether you’re a first-time maker or confident with florals, Clare and Martha will share their artistry, techniques, and thoughtful guidance to help you create something truly special. Clare has worked alongside industry leaders and developed a signature style that blends botanical expertise with artistic expression. Her warm teaching presence makes this experience both refined and wonderfully accessible.

Settle in with a welcome cocktail, delicious light lunch, and soak up the vineyard views as you create, connect, and embrace the festive spirit in a relaxed, inspiring environment.

$275pp

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!

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.

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!

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.

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!

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!