What began in 2024 with little over 20 theatrical events, has morphed to more than 300.
It's expansion beyond the Darlinghurst walls of the city's Centre of Queer History and Culture, Qtopia, has involved a takeover of the entire precinct.
Community demand for the best of LGBTQI arts, culture and theatre is behind the huge growth, festival director Carly Fisher told AAP.
"We are trying to give the community another way of engaging with their pride," she said.
"The desire is there and Pride Fest is the result of that ... we want to make the whole area really buzz again."
Oxford Street has witnessed the closure of multiple iconic venues in the last few years such as the Stonewall Hotel which entered voluntary administration just three weeks after Mardi Gras.
In 2025, Australia's biggest gay nightclub, ARQ, met the same fate after more than a quarter of a century of trading, while the much loved Bookshop Darlinghurst closed its doors for the last time in December.
The retailer had been part of Oxford Street's furniture for more than 40 years, and was closed after a proposed redevelopment faced multiple delays.
Many establishments along the strip have struggled in the aftermath of Sydney's 2014 lockout laws and are also trying to recover from COVID lockdowns.
"These are businesses that have tried to power through more than a decade of laws that are working against them," Ms Fisher said.
But she also acknowledged the next generation of queer Australians was showing their pride differently than those .
Pride Fest has introduced a fitness stream for the first time, to help accommodate young people who prefer pilates over parties.
"It's our responsibility to make sure younger generations know about the history and how they have the rights that they do now," Ms Fisher said.
"We talk about the significance of the 78ers but the way to get the younger generation interested is to make them feel involved as well.
"It was really important for us to ensure that however people want to turn up there was opportunity for them to do that ... everyone needs to find their way of showing pride."
The month-long festival will kick off on June 2 with the inaugural Pride Fest Gala and events will be staggered at venues including The Loading Dock Theatre, The BWYASSS Substation, The Eternity Playhouse, Ginger's at the Oxford and Universal Upstairs and Downstairs.
Headliners include Skank Sinatra and Kala Gare, and Ms Fisher noted the significance of performances taking place in what was once a place where queer voices were silenced.
Qtopia Sydney, the largest queer cultural centre and museum in the world, is housed in the heritage-listed former Darlinghurst Police Station.
"People are performing in a police station that tried to minimise the voices of the LGBTQI community and we've turned it into a place of music and celebration and laughter," she said.
"There is something special about telling your story here because this place was trying to suppress voices and we are amplifying them."
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