Local driver Angus Clydesdale in a 1499cc Gemini race car (number 81) at the 1964 Grand Prix race at Upper Thomson Road, Singapore

2) Pulau Tekong was once home to bustling migrant communities, even during World War II

These days, Pulau Tekong is the predetermined spot for most of Singapore’s young men to undergo national military service. In the past, however, it was home to migrant communities who thrived as Singapore entered the 20th century; many of them also survived the harsh conditions of the Japanese occupation of World War II.

In an episode of  Tourism in 1960s Singapore, it’s revealed how Singapore’s neighbouring islands, Pulau Tekong and Pulau Ubin, had their own bustling residential villages far away from the city. Migrants of Malay, Chinese, and Indian descent had settled there as far back as the 1850s (by the 1980s, Pulau Tekong’s population of 8,000 consisted mainly of Malays, with a few Teochews and Hakkas). In the process, villages had begun to specialise in agricultural and fishing produce, and this was later expanded, under colonial rule, to rubber and farm trade.

Islanders at the opening of Pulau Tekong Kechil Community Centre by Prime Minister Lee Kuan Yew during his tour of the Southern Islands in 1963

Kampung Lorong Buangkok

4) Raffles Hotel boasts many iconic personalities as its past guests

Singapore’s status as a cultural hotspot took decades to form, but a monumental, catalysing event for that development was the opening of Raffles Hotel in 1887.

Upon its inception, the luxurious building played host to a revolving door of distinguished guests for decades.

Raffles Hotel survived both the Great Depression — which caused the property’s founders, the Sarkies Brothers, to go bankrupt and forfeit the hotel — and the Japanese occupation. In the post-war 1950s, cultural icons were more interested than ever in visiting Singapore, and Raffles Hotel became a home away from home.

Modern-day Raffles Hotel

5) Bugis Street used to be an iconic (and colourful) party paradise

On Singapore’s reputation as a world-renowned business hub, Professor Tommy Koh says: “Your influence depends not just on how big your country is in the world but how good you are.”

Over the decades, this bit of wisdom has been applied to different areas of Singapore’s growth. And despite the country’s conservative norms, this has also included its nightlife scene.

From the 1950s to 1980s, what made Singapore an enduring party destination for tourists of a certain inclination — think sailors, bachelors, artists, and the like — was Bugis Street. The neighbourhood, boasting hawker delicacies and al fresco bars, was a lively playground for adults. Regulars here enjoyed the many offerings of the street, including the company of local transgender hostesses, who were, by most accounts, ravishing in appearance, charming by nature, and masterful at their job.

Their work involved entertaining these visitors, and it resulted in wild, all-nighter parties in the area that were extinguished once the 1980s arrived. By then, the government unveiled an urban redevelopment plan that swept the debauchery of the street under the rug. Now a shopping hotspot for tourists and locals alike, the legend of Bugis Street has been kept to the pages of history, while other nightlife districts such as Clarke Quay and Club Street have since grown in repute.

Fun fact: Bugis Street was the subject of the Leonard Cohen song “Boogie Street”, which was the nickname of the area given by its regular visitors. In a 2001 interview, Cohen revealed that during his visit to Bugis Street, he was amused to find bootleg copies of his albums for sale.