A month-long celebration of queer creativity and culture

A cornerstone of Sydney's Pride Month calendar, Pride Fest offers a month of dazzling works and moving stories that celebrate the astounding talent of the LGBTQIA+ community

TRANS GLAMORE is a night to celebrate transgender performers & friends. Launched in August 2017, by the amazing Victoria Anthony. Everyone is encouraged to join in the fun with amazing performers to entertain you each month!

Come join host the fabulous Lada Marks and her guests to celebrate the transgender community. Showtimes 9.30 and 10.30pm. The amazing DJ Victoria Anthony from 9 - close. And hey...you never know who you might meet at the bar!

Thursday 5th June
Where: Stonewall Hotel
Time: 9pm – 11:30pm

PENELOPE PETTIGREW & ANDREW CHARA

When powerhouse pop diva PENELOPE joins forces with piano virtuoso and vocal chameleon ANDREW CHARA, expect a show that’s nothing short of electric. With over 30 years of combined experience lighting up stages across Australia and beyond, this dynamic duo brings together soulful keys, irresistible vocals, and a shared passion for live performance that turns every show into an unforgettable celebration.

For one night only, PENELOPE and ANDREW will be honouring their two greatest musical inspirations—Barbra Streisand and Billy Joel—in a spectacular live tribute show that blends timeless classics with bold new energy. Expect powerhouse vocals, iconic ballads, sing-along anthems, and all the show-stopping charisma these two are known for.

Friday 6th June. Arrival 6pm sharp.

Three Sisters Social Group invites you to Thriller the Soirée, the culmination of the Blue Mountains Pride weekend. Night creatures call. And the dead start to walk in their masquerade. There’s no escaping the jaws of the alien this time

Join us for an evening of fun, food, drink, music, entertainment and perhaps a bit of sci fi horror. Or maybe you will be the monster we are all fleeing. And Flash Gordon was there. In silver underwear

Tickets $99+bf early bird, $109+bf full price

Sunday 8th June
Where: Victoria & Albert Guesthouse, Mt Victoria
Time: 5pm – 9pm

3 courses from our new a la carte menu and 2 live sets $125.

​Ethan has performed in a variety of roles across theatre, film, and television. Most recently, he has taken the lead as producer of On Air Snack Bar, an exciting new podcast that offers an in-depth exploration of the Australian arts industry, featuring insightful conversations with key figures shaping the landscape.​

Alex’s theatre credits include Definitely Not A Hungry Game: A Parody Musical (Dramafreak Productions, Sydney Fringe Festival + Adelaide Fringe Festival), Ignite Before Christmas (Ignite Theatre Company), Carrie (Ignite Theatre Co.), Next to Normal (Whimsical Productions), Girl Shut Your Mouth (Theatre Travels), 1984: The Musical (Independent), Damn Yankees (Brent Street), The Drowsy Chaperone (MUSE) and Inner West Side: The Musical (UltraCult). In 2023, Alex began performing in regular improv comedy shows across Sydney and in 2024 became a victor of the Improv Comedy Cagefight Cup.

17 June. Arrival 6pm sharp

3 courses from our new a la carte menu and 2 live sets $125.

All aboard for a musical trip with Sydney’s only singing train driver. Rob will take you on a melodic journey via many different musical styles. While he will always treat you to a hearty dose of swing you might also stop at some unexpected stations along the way. Think Michael Bublé meets Michael Jackson via Van Morrison with a side of Peter Allen. Rob will drive you through a night of songs, stories and laughs, with perhaps a quick stop work meeting along the way so you can tuck in to the delicious food available. Rob has been singing and playing violin since the age of six, but now he is all grown up and has his licence to drive an audience wild with delight at one of his unique cabaret shows in this distinctive venue.

26 June. Arrival 6pm sharp.

3 courses from our new a la carte menu and 2 live sets $125

After a sensational debut at Claire’s in 2023, Brad returns for an unforgettable night of music and storytelling. Experience his passion for Broadway as he takes you on a journey through a handpicked playlist of iconic shows, beloved artists, and personal moments from the heart of the Big Apple. Don’t miss this intimate and electrifying celebration of musical theatre!

13 June 2025. 6pm Sharp

3 courses from our new a la carte menu and 2 live sets $125.

Kings Cross to Kabukicho: A Wild Singer’s Tale

Kings Cross to Kabukicho – A Wild Singer’s Tale takes you on a wild, glamorous, and unexpected journey through the highs and lows of an Aussie singer’s life on the world stage. From smoky late-night gigs in Sydney’s infamous Kings Cross to the neon-drenched clubs of Tokyo’s Kabukicho, this show blends music and storytelling like no other. With songs from my Just Breakaway album (released through Toshiba EMI), iconic tracks from Konami’s Dance Revolution, French classics from my childhood, and the sultry sounds of Tokyo’s underground scene, this is an unforgettable night of music, intrigue, and reinvention. Expect dazzling moments, jaw-dropping stories, and a celebration of a life that’s been anything but ordinary. Book now—because some stories have to be heard to be believed!

20 June. Arrival 6pm sharp.

Malebox Special Pride Event. Malebox has been going for 27 years every Wednesday at Stonewall Hotel. Charity fundraiser event gold coin donation. Hosted by Marilyn Mootrub and Maleman Pablo. Amazing DJ’s and more.

Grab a number, send a message and Sydney’s premier pick up night.

Join us on Wed 25th June from 9pm

3 courses from our new a la carte menu and 2 live sets $125. Arrival 6pm sharp

Karen Jacobsen performs one night only at Claire’s Kitchen while on the go between her former New York City home and new paradise retreat in the Whitsundays.

You will be entertained by hilarious stories and listen to timeless, melody-driven songs while being uplifted and inspired by Karen’s powerful vocals. She has enjoyed wide international media attention; Harry Connick Jnr called her “hypnotic” on his national U.S. talk show, she has been a clue in The New York Times crossword puzzle, and you can expect a classic Claire’s evening of sparkling entertainment by an artist who has shared the stage with Norah Jones, Christopher Cross, Cyndi Lauper, Jon English and Toni Childs.

27 June 2025. Arrival 6pm sharp.