Our 2026 calendar brings together the events you know and love, alongside fresh new experiences designed to delight, entertain and surprise. Expect unforgettable performances, exceptional dining, outstanding musicianship and moments that will have you laughing, applauding – and coming back for more.
Whether you’re celebrating with family, catching up with friends, or entertaining colleagues, there’s always something special waiting at the Castlereagh.
We look forward to welcoming you in 2026 with your friends and family!
Join us for a special Wines of the World evening in the elegant surrounds of Cellos Grand Dining Room, hosted by renowned wine industry figure James Herriott. Guests will enjoy a beautifully curated five-course menu, expertly paired with premium wines from France, Italy, Germany and Portugal, including Champagne, Burgundy, Barbaresco, Riesling and 10-Year-Old Port.
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Straight from London’s West End via the legendary Sydney Opera House, this international sensation is now returning to Castlereagh Boutique Hotel in 2026. Officially the world’s most sought-after tribute to the BBC sitcom, Faulty Towers The Dining Experience is simply unmissable – and ‘outrageously funny’ (BroadwayBaby)!
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Join a 1930s Christmas in July murder mystery dinner - dine, gather clues, and solve the chilling case of Yule Be Sorry! Whilst you enjoy a delicious three course dinner, gather clues from the various suspects as they visit your table, discuss with your fellow diners and then decide...whodunnit!
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The Fabulous Fifties Fashion Show. Step back into the glamour and sophistication of the 1950s with an evening celebrating one of the most stylish decades in fashion history. Presentation by The Cavalcade of History & Fashion followed by 1950s styled cocktails and ‘hors d’oeuvres’.
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The worst wedding reception you’ll ever go to… and everyone is invited! It was meant to be a surprise party to celebrate Will and Stacey’s wedding, but it’s turned into pandemonium – with secrets spilling out as uninvited and misbehaving family members bust in, bust up and bust a move. Audiences become guests caught in the crossfire in this totally immersive and highly improvised comedy.
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FREE ENTRY | Chapel Row Jazz is hosted weekly by Alex Putra, bringing a rotating lineup of Sydney’s next-gen jazz talent to the Reagh Bar. Each Friday, Alex is joined by friends and collaborators from across the city’s live music scene creating a set that’s spontaneous, high-energy, and never the same twice.
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Experience Sydney's most enchanting night out with The Gentleman Magician’s Magical Soirée at the Castlereagh Boutique Hotel. World-class magic, captivating stories, and timeless elegance - every Friday and selected Saturdays. Book now!
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This is a gorgeous old world hotel and the service was impeccable. Everything about the hotel we loved...
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