What's On at Cupitt's

Cupitt's hosts live music every weekend, with the exception of the following dates when we are closed for private events.

Friday 21st February

Tuesday 11th March

Friday 14th March

Friday 21st March

Friday 28th March

Friday 4th April

Friday 11th April

Friday 2nd May

Thursday 8th May

Thursday 14th August

Thursday 28th August

Thursday 6th November

Monday 17th November

Join us for a Golden Saturday Session at the Winery, featuring local Ulladulla legend, Guy Turk. Let the soothing sounds of Guy’s original tracks, along with timeless favourites, set the perfect vibe as the sun dips beyond the Estate.

Relax with a glass of our estate-made wine in hand, indulge in a sunset dinner, and unwind to live music as the weekend unfolds. The kitchen will be serving up delicious dishes until 7pm, so gather your friends and family, grab a table, and make it a night to remember!

Ease into your Sunday with the soulful sounds of Cassidy Bird (Cassy Rae). A solo artist, rhythm guitarist, and percussionist, Cassy brings feel-good energy and smooth acoustic vibes—perfect for a lazy afternoon in the Wine Garden.

Make a day of it: Book a long lunch in the Dining Room. Drop into the Cellar Door for a wine tasting. Settle in with a drink & share plates in the Wine Garden. Live music, great wine, and summer sunshine—sounds like the perfect Sunday.

Ease into the weekend with live music, golden hour views, and a relaxed evening in the Wine Garden. The Nat Lizak Duo will be setting the scene with their smooth acoustic sound and soulful harmonies—perfect for a laid-back Friday night.

Enjoy a long summer evening with estate-made wine, fresh seasonal dining, and live music as the sun sets over the hills. The kitchen is open until 7pm, so grab a table, order a bottle, and settle in for the perfect start to the weekend. Music from 5pm.

A weekend dedicated to great wine, exceptional dining, and the Cupitt’s community. Join us for a carefully curated lineup of tastings, behind-the-scenes tours, long-table feasts, and intimate experiences with the Cupitt family. Whether you come for one event or indulge in the full weekend, it’s a chance to connect, celebrate, and experience Cupitt’s like never before.

Book now and be part of an unforgettable weekend of wine, food, and good company.

Not a member yet? Sign up for the Cupitt’s Wine Club today to receive exclusive early access to events and news!

Join us for a relaxed four-course dinner paired with rare museum wines from our cellar, reserved for special moments like this. Hosted by the Cupitt family, it’s an evening of great food, live music from Ace Avenue, and behind-the-scenes stories, all in the warm company of fellow wine lovers. We can’t wait to share this memorable night with you!

Book now and immerse yourself in a memorable evening of exceptional wine, delightful cuisine, and wonderful company.

Join us for a festive celebration of the harvest, where good food, great company, and fascinating behind-the-scenes tales await. Gav, our skilled viticulturist, and Wally, our talented winemaker, will share the stories that bring our wines to life.

Indulge in an Italian-inspired feast, designed to pair perfectly with wine, featuring a welcome drink, a seasonal three-course menu, and a sprinkle of trivia fun. $99 per person.

Blues, soul, and a whole lot of groove—Horse Drawn Cadillac is bringing the energy to this week’s Sunday Session in the Wine Garden. With a sound that blends raw blues and deep Southern soul, this is live music made for a laid-back afternoon with good wine, great company, and summer vibes.

Settle in with a long lunch, enjoy a wine tasting in the Cellar Door, or grab a drink and soak up the tunes as the weekend winds down.

Celebrate International Women’s Day with a long-table luncheon at Cupitt’s Estate, bringing together community, conversation, and connection in a truly special setting. This year’s theme, "Accelerate Action," explores the power of resilience, change, and progress. Hear from inspiring guest speakers as they reflect on "What A Difference A Year Makes", sharing stories of growth, transformation, and impact.

Enjoy a mimosa on arrival, followed by a seasonal brunch and shared main course lunch, curated with estate-grown produce and served in the stunning surrounds of the Estate.

Whether you come with friends, colleagues, or join the table solo, this is a chance to celebrate, reflect, and be part of a day dedicated to empowerment and connection.

Tickets $95 per person | Includes welcome drink, brunch, shared lunch, and lucky door prize

Kick back, relax, and let the music set the tone for a perfect Golden Saturday Session with Alex Clarke. With a soulful voice and effortless acoustic style, Alex brings warm, laid-back vibes to the Wine Garden, making it the ideal way to slow down and soak up the weekend.

Enjoy a long sunset dinner, a glass of estate-made wine, and live music as the weekend unfolds. The kitchen is open until 7pm, so grab a table and make a night of it.

Join us Sunday, March 30th, for an afternoon of great vibes with All the Fuss in the Wine Garden! Perfect for a laid-back Sunday with a touch of fiesta—grab a glass of wine, enjoy a delicious lunch, and soak up the sunshine with friends. It’s the perfect way to wrap up the weekend. See you there?

Settle in for a Golden Saturdays session with Ziggy McNeill, an acoustic artist known for his dynamic guitar work, looping mastery, and raw, soulful vocals. Whether he’s blending folk, blues, or a touch of rock, Ziggy’s energy is infectious, making for the perfect laid-back Saturday evening in the Wine Garden.

Enjoy a long sunset dinner, a glass of estate-made wine, and live music as the weekend unfolds. The kitchen is open until 7pm, so grab a table and make a night of it.

Ease into Sunday with Ziggy McNeill, bringing a mix of upbeat acoustic energy and smooth, soulful melodies to this week’s Sunday Session. A true storyteller through music, Ziggy’s looping skills and effortless sound make for a perfect long afternoon in the Wine Garden.

Sit back with a glass of wine, enjoy a relaxed lunch, or pop by for a tasting before settling in for the music.

Ease into the Easter long weekend with a Sunset Session featuring Alex Clarke. With a soulful voice and effortless acoustic style, Alex brings warm, laid-back vibes—perfect for unwinding as the sun sets over the vineyard.

Settle in for a relaxed evening in the Wine Garden, enjoy a wine tasting in the Cellar Door, or make a night of it with dinner and drinks as the long weekend begins. Live music, estate-made wine, and golden hour views—it doesn’t get much better.

All the Fuss are bringing their high-energy acoustic sound to the Wine Garden for a Sunday Session you won’t want to miss. With rich harmonies, dynamic guitar work, and a mix of crowd-favourite covers and originals, they set the perfect tone for a laid-back afternoon with good wine, great food, and even better company.

Make a day of it with a long lunch in the Dining Room, a wine tasting in the Cellar Door, or just grab a drink and settle in for the music. Sunday done right.