Castlereagh Boutique Hotel Events

Join us for some of the most unique Sydney Events!

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!

✫ SOLD OUT ✫ Cavalcade of History & Fashion - 1930s Fashion High Tea

Thursday 16 April, 2.00PM - 3.30PM

Step into 1930s elegance at this fashion high tea. Enjoy a fashion pshow, historical talk & high tea at Castlereagh Boutique Hotel. Delight in the elegance of the 1930s glamorous evening gowns and accessories and hear the stories of the real women who wore these gowns as history is brought to life. A wonderful experience for those with an interest in fashion, history, or simply a refined afternoon out - ladies and gentlemen alike.

Hentley Farm Winemaker Lunch

Thursday 23 April, 12.00pm – 3.30pm

Join us for a fabulous afternoon of wining and dining as we welcome Hentley Farm. Led by James Herriott, National Brand Ambassador for the multi award-winning super premium Barossa wine producer Hentley Farm, this special event is an opportunity to discover a remarkable range of wines in one of Sydney’s most elegant heritage settings.

ANZAC Day Lunch & Commemorative Service

Saturday 25 April, LUNCH 12.00 PM, COMMEMORATIVE SERVICE 3 PM

Join us this ANZAC Day for Lunch and our Commemorative Service. A commemorative luncheon will be served in Cellos Grand Dining Room, after which guests will be led by our Returned Servicemen and Pipe Band into the Reagh Bar for the ANZAC Day Commemorative Service, culminating in the Last Post.

Faulty Towers The Dining Experience

Thursday 7 May, + more 2026 dates!!

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)!

Mother's Day Opera High Tea - featuring Opera Bites

Sunday 10 May, 2.00 - 4.30 pm

Celebrate Mum in style with an Opera High Tea this Mother’s Day! From the stunning chandeliers to the glass of sparkling on arrival, Mum will be pampered from the moment she steps through the doors of our beautiful heritage-listed grand dining room. Expect a unique experience to cherish with arias and ensembles from the world’s most adored stage-works brought to you in fully costumed splendour.

Cluedunnit Murder Mystery Dinner - YULE BE SORRY

Saturday 18 July, 6.30PM - 9.30PM

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!

Confetti & Chaos - Comedy Dinner Show

Saturday 22 August, 6.30pm arrival, 7pm start

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.

Chapel Row Jazz - Every Friday

Friday 20 February, Then Every Frday from 7pm - 10pm

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.

The Gentleman Magician’s Magical Soirée

Friday 30 May, EVERY FRIDAY FROM 7.00PM

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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