What's On at Cupitt's Estate

NOVEMBER - 6th, 17th, 25th

DECEMBER - 25th, 26th

2026

FEBRUARY - 20th, 27th

MARCH - 5th, 13th, 30th, 26th

Cellar door is open from 9am until 1pm for sales and 11am to 12:30pm for tastings

Ease into your Sunday at Cupitt’s Estate with the enchanting sounds of The Castaways, an acoustic duo weaving together pop, folk, country, and blues into a perfectly mellow soundtrack for your afternoon. From 12:30pm to 3:30pm, let their rich harmonies carry you across the vineyard, with Burrill Lake and the Budawang Mountains providing the ultimate backdrop. Whether you’re lounging with a glass of wine, catching up with friends, or enjoying some quality family time, The Castaways’ warm, soulful tunes will make your Sunday feel a little slower, a little sweeter, and entirely unforgettable.

For one special evening, the rolling hills of Milton will feel just like Tuscany. Join Cupitt’s Estate and Lowe Family Wines for an unforgettable dinner celebrating the charm and character of Italian varietals grown right here in NSW.

As part of NSW Wine Month, this event brings together two of the state’s most passionate wine families — with guest chef Kim Currie fromMudgee’s acclaimed Zin House joining forces with our Cupitt’s kitchen to create a six-course feast inspired by the Italian table.

Across six courses and six wines, you’ll taste why Italian grapes thrive on our local soils — from sparkling Prosecco and crisp Vermentino, to aromatic Arneis and the soulful reds Sangiovese, Primitivo, and Nebbiolo. Each pairing has been carefully crafted to showcase both varietal character and its unique NSW expression.

Hear stories from David Lowe, Rosie Cupitt and Wally Cupitt as they share their winemaking journeys, their passion for Italian varietals, and why they believe NSW is the future home for these beloved grapes.

With vineyard views and the warmth of good company, this is the ultimate pre-Christmas catch-up and a true celebration of Italian spirit on Australian soil.

Tickets: $200pp

Includes a six-course dinner with matched wines.

One night only – Wednesday, 12 November

There’s nothing quite like a Sunday at Cupitt’s Estate — good wine, great company, and live music drifting across the vines. This week, we’re thrilled to welcome The Specialities, a five-piece band known for their seamless blend of blues, jazz, soul, and alt-country. From 12:30pm to 3:30pm, settle in on the lawn or the deck, take in the sweeping views over Burrill Lake and the Budawang Mountains, and let their smooth, soulful sound set the tone for a perfect afternoon.

All the Fuss are back this Sunday, 23 November, 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!

Cupitt's Estate will be closed on the 25th of November as we take time to celebrate our incredible team at our annual Christmas party. It’s a moment for us to come together and reflect on the year's achievements before the busy holiday season begins. We appreciate your understanding and look forward to welcoming you back the following day.

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!

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!

A family friendly Christmas sunset session with live music by the talented Harmony Music.

More details to come...

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!

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!