Centuries ago, Malay kings ruled from its peak. Huddled in a bunker there, British army officials made the fateful decision to surrender Singapore to the Japanese during World War II.
Today, Fort Canning Hill is undergoing another transformation. Come May, the three-storey building at its heart, now called Fort Canning Arts Centre, will be unveiled as a 5,480 sq m offshoot of Paris' largest private art museum, its first outside of France.
The Singapore Pinacotheque de Paris is steered by art historian Marc Restellini, founder of the esteemed Paris institution. It showcases Western and international art masterpieces through the ages by the likes of Botticelli, Rembrandt and Picasso, on loan from private collectors worldwide.
Besides galleries with interactive displays allowing visitors to download information on the physical artworks into their mobile devices, the Singapore museum will also house a heritage gallery of Fort Canning and an art academy conducting art history and appreciation courses.
Details of the space were revealed by the Paris-based Mr Restellini to Life! during his visit here this week.
Renovations to the Fort Canning building, previously a cluster of arts studios and offices, began in January and will be completed in four months.
He promises that, as with the Paris museum, there will be "a lot of beautiful things here". About 40 to 50 works from the museum's collection will be on display in a ground-floor permanent gallery.
There will also be rotating exhibitions curated with Mr Restellini's signature approach of "transversality", fleshing out connections across artists, eras and cultures. While the opening show for the Singapore museum will be announced at a later date, shows at its 11-year-old Paris counterpart have ranged from a look at how Van Gogh was inspired by Japan to exploring the American abstract expressionist Jackson Pollock's link with shamanism.
Where the Singapore museum differs from the Paris one is in its economic model. "In Paris, a lot of our income comes from ticketing - we have more than one million visitors a year. In Singapore, we have to develop other processes of income," Mr Restellini says.
Hence the basement of the Fort Canning space will have food and beverage and retail tenants, while its art academy will have different types of courses and lectures catering to the public, art students as well as private collectors and corporations.
Mr Restellini, who chose the site because of its rich history, says his vision is "to embrace its heritage while marrying the vision of the future".
In line with that, a heritage gallery on the ground floor is being developed with local history experts.
While ticket prices to the museum are still being finalised, he says admission to the heritage gallery is free.
Beyond the museum, the aim is to turn Fort Canning into a lifestyle destination, says Ms Suguna Madhavan, chief executive of Art Heritage Singapore, the company running the Singapore Pinacotheque de Paris.
"We have a fantastic location, we are a hidden gem just a staircase up from Park Mall in Orchard Road. We need only to make people aware and bring them up the hill by giving them different points of interest, be it an exhibition, lunch or courses," she says.
Art Heritage Singapore is a partnership between Mr Restellini, local integrated investment company KOP Group, Singapore Diamond Exchange chairman Alain Vandenborre and Singapore Freeport chairman Yves Bouvier.
Beyond the four walls of the museum, Ms Madhavan says it intends to work with partners to stage arts events in Fort Canning Park.
"We're going out to the community, as opposed to saying, 'We are the museum, come to us,'" she says.