What's On at Cupitt's Estate
Live music & special events every week

There’s always something happening at our place! From weekly live music sessions and seasonal events to updates on special experiences and days we're closed, this is the best spot to keep up with what’s going on. Whether you're planning a relaxed visit with friends or looking to join one of our signature events, you’ll find all the details you need right here. Check back regularly so you don’t miss a beat!
Mid-week in June
Local's Lunch
Dine with us mid-week this June and enjoy our lunch special.
Duck ragu with pappardelle $29*
Add a glass of wine for $10
Lunch Mon - Fri - either in the Dining Room or Wine Garden
*Special menu item is subject to change.
Venue Closed
AUGUST - Thursday 6th and Friday 28th
Stay tuned for this week's activity I 5 - 6pm
Family Friday I 19th June
Family Meal Deal – Just $75
Two pizzas, a fresh salad, a jug of soft drink + your choice of two glasses of house wine or beer.
While the kids play, adults can unwind in the Wine Garden with a drink in hand and soak up the sunset and beautiful vineyard views.
Bookings are great but not required - just bring the family, get comfy, and enjoy the best of local food, wine, and community vibes.
Stargazing | 6.30pm
Sip Under the Stars | 20th June
A Night of Wine, Cheese + Stargazing | 1 hour
Embark on a captivating space journey, vino in hand. Experience this one-of-a-kind stargazing night. Indulge yourself with wine and cheese on arrival under the stars, a stargazing session led by an astronomer and exploration of the Southern Sky - planets, galaxies, stars, constellations and galaxies through the telescope.
You can then book in to dinner from 7.30pm for a cozy dinner in the Dining Room.
Sunday Session | 12:30pm
Josh Rawiri| 21st June
Settle in for a relaxed Sunday afternoon of live music, great wine, and good company at Cupitt’s Estate.
Join us from 12.30pm on Sunday 21 June as Josh Rawiri takes to the lawn. An Australian singer-songwriter known for his heartfelt performances, Josh blends folk, soulful blues, roots rock, and reggae into a sound that is both laid-back and captivating.
Gather your friends, order a long lunch, pour a glass of your favourite Cupitt’s wine, and enjoy an afternoon of live music overlooking the vineyard.
Sunday Sessions | 12:30pm
The Specialties | 28th June
Unwind among the vines with a glass of Cupitt’s wine in hand and a selection of delicious seasonal bites, as live music sets the tone for a perfect Sunday.
Join us on June 28 for an afternoon with The Specialities—a talented five-piece blending blues, jazz, alt-country and funk. Led by award-winning saxophonist Wayne Rigby and featuring Shannon Carswell on vocals, Shawn Supra on double bass, Nic Lewis on guitar, and Willem Van Ekert on drums, their soulful sound is the perfect match for a laid-back afternoon.
Gather your friends, soak up the views, and enjoy great wine, great food, and even better music.
Sunday Session I 12.30pm
Richard and the Lionhearts I 5th July
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.
Come for the great music, stay for the vibes and end the weekend with a glass of Cupitt's wine and delicious bites.
Stargazing | 6.30pm
Sip Under the Stars | 11th July
A Night of Wine, Cheese + Stargazing | 1 hour
Embark on a captivating space journey, vino in hand. Experience this one-of-a-kind stargazing night. Indulge yourself with wine and cheese on arrival under the stars, a stargazing session led by an astronomer and exploration of the Southern Sky - planets, galaxies, stars, constellations and galaxies through the telescope.
You can then book in to dinner from 7.30pm for a cozy dinner in the Dining Room.
Sunday Session | 12:30pm
The Stayers | 12th July
Spend your Sunday afternoon at Cupitt’s Estate with great food, outstanding wine, and live music from The Stayers. Bringing their signature blend of soulful songwriting, bluesy grooves, and laid-back energy, The Stayers create the perfect soundtrack for a relaxed afternoon on the estate.
Settle in with a glass of wine, enjoy something delicious from the kitchen, and soak up the atmosphere as the music rolls on.
Good wine, great company, and live music done right. We’ll see you there!
Sunday Session | 12:30pm
Keith Zehr | 19th July
Join us and local musician Keith Zehr! Live music from 12:30 pm to 3:30 pm, enjoy live music and long lunch amidst the stunning views of our vineyard, Burrill Lake, and the Budawang Mountains. Sundays at Cupitt's are all about live music, great vibes, and happy faces.
Whether you're a local or just visiting the South Coast, come for an afternoon of delicious food, great tunes, and an incredible atmosphere. We're also dog-friendly; all welcome; the more, the merrier!
Christmas in July Theme I 5 - 6pm
Family Friday I 24th July
Come and celebrate the magic of winter this Christmas in July at Cupitts! Christmas themed face painting and more.
Family Meal Deal – Just $75
Two pizzas, a fresh salad, a jug of soft drink + your choice of two glasses of house wine or beer.
While the kids play, adults can unwind in the Wine Garden with a drink in hand and soak up the sunset and beautiful vineyard views.
Bookings are great but not required - just bring the family, get comfy, and enjoy the best of local food, wine, and community vibes.
Sunday Session | 12:30pm
Amy & I | 2nd August
Local duo Amy & I, featuring Amy Smith and Simon Kinch, are excited to bring their shared love of music to Cupitt’s Estate for a relaxed Sunday Session.
With an acoustic folk-inspired sound, Amy & I reimagine a selection of favourite songs alongside original material, blending keys, guitar, and rich vocal harmonies with effortless synchronicity.
Gather your friends, settle in for delicious bites and a glass or two of Cupitt’s wine, and end the weekend on a high.
Friday Sunset Session | 4pm
Tall Shaun | 7th August
Join us for a relaxed Sunset Session with live music from Tall Shaun this Friday 7th August, as you unwind among the vines.
This is Friday done right — unhurried, open-air, glass in hand, with the kitchen serving up seasonal dishes and music that feels made for golden hour. Tall Shaun’s original blues and alt-country sound brings a soulful, easy rhythm to the evening, carrying you from sunset and well into the night.
Come settle in, take in the views, and ease into the weekend the Cupitt’s way.
Stargazing | 6.30pm
Sip Under the Stars | 8th August
A Night of Wine, Cheese + Stargazing | 1 hour
Embark on a captivating space journey, vino in hand. Experience this one-of-a-kind stargazing night. Indulge yourself with wine and cheese on arrival under the stars, a stargazing session led by an astronomer and exploration of the Southern Sky - planets, galaxies, stars, constellations and galaxies through the telescope.
You can then book in to dinner from 7.30pm for a cozy dinner in the Dining Room.
Sunday Session | 12:30pm
Minnie and the Moonrakers | 9th August
Warm up your Sunday afternoon at the winery with the infectious sounds of Minnie & The Moonrakers. From 12:30pm, the band brings a lively, toe-tapping mix of ‘50s rock ’n’ roll, swampy blues, swing, and rockabilly to the stage.
Settle in with a glass of wine, something delicious from the kitchen, and let the music carry you through a cosy winter afternoon. With plenty of groove and vintage flair, Minnie & The Moonrakers are the perfect soundtrack for a relaxed day at the winery.
Great wine, great music, and the charm of a winter’s day. We’ll see you there!
Sunday Session | 12:30pm
All The Fuss | 16th August
Get ready for a Sunday session at the winery as All The Fuss return on Sunday the 16th of August! Bringing their signature toe-tapping tunes and laid-back vibes, they’ll have you grooving the afternoon away. Gather your friends, book a table, and settle in for a delicious lunch, great wine, and sunshine-filled afternoon.
Sunday Session | 12:30pm
Fathers Day with Soul Tonic | 6th September
This Father’s Day, show your appreciation for the superheroes in our lives and treat him to a memorable day out at Cupitt's Estate.
Enjoy the soulful sounds of Soul Tonic as they bring their signature blend of smooth grooves, heartfelt classics and feel-good favourites to the stage. Whether performing beloved hits or putting their own spin on timeless tracks, Soul Tonic create the perfect laid-back vibe — guaranteed to have you smiling, swaying and soaking up the moment.
Make the day extra special by booking into the Cupitt’s Estate Restaurant for a beautiful 3-course menu, thoughtfully curated for the occasion. Or reserve a table in the Wine Garden and gather the whole family for a relaxed celebration filled with great music, delicious food and award-winning wines.
Bookings recommended.
Sunday Session | 12:30pm
All The Fuss | 27th September
Join us on Sunday 27th September as All The Fuss return to the winery for another unforgettable afternoon of live music, great wine, and good vibes. With their signature toe-tapping tunes and crowd-favourite jams, they’ll have you grooving the afternoon away. Round up your friends, book a table, and enjoy a delicious lunch in the sunshine while soaking up the sounds of a perfect Sunday session.
