August 16 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
August 30 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
September 11 • 7:30 pm - 10:30 pm C.W. Stoneking Milton Theatre 69 Princes Highway, Milton, NSW, Australia ON SALE THURSDAY 25TH JUNE @ 10AM Lonely Lands Agency presents C.W. Stoneking returns to Australian stages this August and September, bringing his one-of-a-kind brand of hokum blues, jungle exotica, and old-time gospel to rooms and halls across the country. With a voice that sounds like it was conjured from a different era entirely,
September 13 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
Featured September 26 • 7:30 pm - 10:30 pm Ben Lee & Georgia Maq Milton Theatre 69 Princes Highway, Milton, NSW, Australia Craft Music & Select Music Presents BEN LEE & GEORGIA MAQ The “Two Most Annoying People You Love” Tour Ben Lee and Georgia Maq team up for The “Two Most Annoying People You Love” Tour of Australia, September/October 2026 You would be hard-pressed to find two more inspiring, outspoken and provocative figures in Australian music
Featured September 26 • 8:00 pm - 10:00 pm Zach Bryan Tribute Show – Zak Plays Zach Marlin Hotel Princes Highway, Ulladulla, NSW, Australia Zak Plays Zach is the World's #1 Zach Bryan Tribute Show. Capturing the raw emotion, poetic grit, and anthemic energy that has made Zach Bryan one of the most defining artists of the modern Country Music era. Led by Zak Shepherd, ZPZ (as it is now known as) has rapidly become a fan favourite for
September 27 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
Featured October 2 • 7:00 pm - 10:30 pm Diesel Milton Theatre 69 Princes Highway, Milton, NSW, Australia DIESEL’s ‘BY REQUEST’ tour returns to regional NSW & VIC, offering a one-of-a-kind conversation between artist and audience. Opening the door for fans to shape the night, the show delivers career-spanning, hit-filled evenings powered entirely by audience requests. With song choices on offer ranging from the debut album - 1989’s Johnny Diesel & The Injectors,
October 11 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
Featured October 17 • 7:30 pm - 10:30 pm Sydney Comedy Festival Showcase Milton Theatre 69 Princes Highway, Milton, NSW, Australia Sydney Comedy Festival presents Sydney Comedy Festival Showcase Tour: THE FESTIVAL'S FUNNIEST IN ONE HILARIOUS NIGHT! The Sydney Comedy Festival Showcase tour will be tearing up the freeways of Australia to bring the best of the 2026 Festival! Expertly curated and lovingly presented, the Showcase will feature some of the Festival’s hottest acts live on stage
October 25 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are
November 8 • 12:30 pm - 3:30 pm Cupitt’s Estate Sunday Sessions Cupitt’s Estate Sunday Sessions Cupitt's Estate 58 Washburton Road, Ulladulla, NSW, Australia Come along every second Sunday for some free live music at Cupitt's Estate. Enjoy the Estate made wine, craft beer, and delicious food while singing along to their fabulous local talent who play with a backdrop of the green rolling hills of Milton, the Budawang ranges and Burrill Lake. Bookings for the Terrace tables are