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  • Writer's picturelionheartlanders

Landmarks Of Singapore- A Heritage Trail Of Orchard

Updated: May 19, 2022

Affectionately known as the “Shopping District Paradise”, featuring our country’s tallest shopping mall, and luxury brand outlets in every direction, Orchard Road is arguably one of Singapore’s most popular regions.

With the street illuminated by thousands of dazzling lights during Christmas every year, and with buildings fighting for the “Best Dressed Building” award, Orchard Road is a sight to see for tourists and locals alike.

From an unnamed road home to pepper farms and nutmeg plantations, to one of the busiest streets in the whole nation, come and find out how Orchard had a complete makeover in just 50 years!

1.Old Cathay Building

Old Cathay Cinema
Photo credit: NLB eResources

As the first and tallest skyscraper in Singapore and in Southeast Asia, this 16-story building was first revealed in 1939 and consisted of a restaurant, a dance hall on the ground floor, along with a residential storey block with a penthouse.

And of course, the Cathay Building featured a Cathay Cinema, Singapore’s first-ever cinema, and was an immediate hit among the local residents.

Eventually, an 11-storey residential block was opened for occupancy, with the owners Mrs. Loke Wan and Loke Wan Tho, The founders of the Associated Theatres Ltd (which was later renamed Cathay Organisation), occupying the top floor.


By early 1941, the Cathay building was one of the last few places around for relaxation, with the cinema still screening movies despite the dwindling audiences and the impending terrors of the upcoming war.

With the war at hand, the building was rented out to the government and the British Malaya Broadcasting Corporation.

Five floors were occupied by broadcast studios and administration, and two floors by the Ministry of Economic Warfare, while the Royal Air Force occupied two rooms on another floor.

In February of 1942, when the Japanese accelerated their attacks on Singapore, the radio station broadcast updates on enemy advances from their studio in the building. It has been estimated that the building was hit by at least 14 shells in that month.

Eventually, when Singapore fell to Japan, the Cathay building was where the Japanese flag was first flown as one of the conditions of the British surrendering.


The Japanese Broadcasting Department then moved into Cathay Building and took over the existing broadcasting facilities.

In March 1942, the department began transmissions of Radio Syonan from there. Later, their Propaganda Department Headquarters and Military Information Bureau were also relocated there.

The restaurant became a dining room for the Japanese military officers stationed in the building.

Outside the building, there were human heads stuck on poles; these were beheaded looters and other victims of the Japanese military.


When the war was over, former staff members all came back to help reopen the cinema.

Cathay Hotel
Photo credit: Alamy

By 1954, they opened a hotel, naming it “Cathay Hotel”, with the 10 floors formerly part of the hotel being converted into office premises.

It initially opened with only 60 rooms but after booming success, expanded to 170 rooms, and was one of the prime meeting places for celebrities, tourists, and families alike. Some amenities included a restaurant, nightclub, swimming pool, and shopping arcade.

The hotel eventually closed down in 1970.


On 10 February 2003, the Cathay building, along with the Macdonald House, became the first to be gazetted under a new monument preservation scheme, which allowed partial redevelopment of historical buildings that were privately owned.

And finally, on 24 March 2006, the now former Cathay building was redeveloped and officially opened as The Cathay.

The Cathay
Photo credit: The Best Singapore

2. Orchard Road Presbyterian Church

Orchard Road Presbyterian Church
Photo credit: RootsSG

Built in 1878, The Orchard Road presbyterian Church, also known as “Greja Kechil,” is the oldest presbyterian church in Singapore and the oldest church on Orchard road.


The church originally comes from the congregation of the Mission Chapel of Singapore and consisted mainly of members of the Scottish community.

In 1822, the Scottish members held a meeting in order to set up a local Presbyterian church for them to attend.

The first recorded service was finally held at the London Missionary Society’s chapel on Bras Basah Road, and the services after were held at the St Andrew’s Church.

Finally, in 1875, a piece of land on Orchard Road was allocated by the Governor of Singapore allowing them to use it for the construction of the church, and the foundation stone for it was laid by Colonel Anson on the 1st of August 1877.

The building was eventually completed in 1878.


Orchard Road Presbyterian Church
Photo credit: Gathered+Styled

The church was designed in a simple but elegant style, a single-storey structure with tiled pitched roofs, and a Palladian-styled facade facing Orchard Road.

The most outstanding feature of the facade is the Serlian Motif, a central arched opening flanked by openings on either side with flat entablatures.

The church also has one of the few working pipe organs in Singapore.

3. Red Cross House

Red Cross House
Photo credit: RootsSG

The Singapore Red Cross is one of the biggest humanitarian organizations in Singapore, that is part of a worldwide, non-political, and non-religious international Committee of the Red Cross.

Founded on 30th September 1949, the Singapore Red Cross provided crucial first aid, social welfare, and relief services in the years much before these same services became widely available in Singapore.

The society and its members operated from various numbers of temporary locations, before it moved to its current building, the Red Cross House.

Officially opened in 1961 by our former president Mr. Yusof Bin Ishak, who was also the then Patron of the SRC.

The Red Cross House was initially built as a two-storey building with a boomerang-shaped canopy over its main entrance, and a third storey was eventually added in the 1970s.

The building was eventually conserved in 2014.


Red Cross
Photo credit: Redcross Youth

Today, the SRC boasts a number of 4,500 members throughout our little island, pledging to provide relief services for all who are in need.

The Red Cross House also provided in-house tours in March of 2019, for their 70th anniversary, for locals to experience their rich heritage, learn first aid, and even ride an ambulance!

4. Ngee Ann City

Ngee Ann CIty
Photo credit: RootsSG

Ending off with one of the most popular shopping spots in Orchard, Ngee Ann City is located right at the heart of Orchard Road and is a hotspot for the young and old alike.

Carrying many branded boutique stores such as Chanel and Fendi, as well as the ever popular Japanese Department Store, Takashimaya.

However, what many are unaware of is that this very spot was where a cemetery once resided.


Ngee Ann City
Photo credit: The Smart Local

In the 1950s, the land where Ngee Ann City sits was a Teochew burial ground called Tai Shang Ting. With over 72 acres and 30,000 graves, this cemetery was owned by Ngee Ann Kongsi.

To make way for the development of his shopping district, he started exhuming the cemetery in the early 1950s, and the exhumed remains from the cemetery were later interred at the Teochew Memorial Park at Yishun.

Finally, in 1957, he opened the first building completed on the site of the former cemetery, a 10-storey building was housed apartments and shops alike.


It comes as no surprise that a former burial ground turned shopping mall has its fair share of ghost sightings.

An employee of Ngee Ann City once claimed to have heard a female voice a couple of times inside his hotel room, and the faucet in the toilet was turned on fully twice.


Ngee Ann CIty
Photo credit: The Shop City

Ngee Ann City has two main office towers, Tower A and B, which both are 26 stories high.

And among its many shops would include a Kinokuniya, the second-largest bookstore in Southeast Asia and a fan favorite among many book lovers all across Singapore.

Ngee Ann City certainly has something for everyone, and rightfully remains one of every Singaporean's choice shopping malls across Orchard Road.

5. Tangs Plaza

Ngee Ann City Building
Photo credit: Time Out

Just opposite Ngee Ann City lies the “Imperial Palace” of Orchard Road, Tangs Plaza.

A five-storey building based on the Imperial Palace in Beijing, China, Tangs Plaza or also just known as Tangs, is a popular departmental store owned by C.K. Tangs limited.

The store is regarded as a principal shopping destination in our country, a well-loved and patronized mall by everyone alike.

Tang Choon Keng
Photo credit: Pinterest

Tang Choon Keng, or affectionately known as C.K. Tangs, was a Singapore entrepreneur and the founder of Tangs Plaza.

Emigrating from China with just a pair of tin trunks containing Chinese hand-embroidered linen, Mr. Tangs story is truly a Singaporean from rag-to-riches story.


Born in Swaton China to a Presbyterian pastor, Tang first arrived in Singapore in 1923.

He had initially made a living through peddling hand-made Swatow lace and embroidery door-to-door from a hired rickshaw.

After almost a whole decade later, Tang saved up enough funds to start a larger venture.

Now with a reputation for stocking traditional Chinese handicrafts, he used $3,000 and opened his first retail store on the first floor in a building on Singapore’s River Valley Road in 1932.

Eventually, he built another building at the corner of Jalan Mohamad Sultan and River Valley Road.

Gainurn Building
Photo credit: Commercial Guru

Naming it after a variation of his father’s name, Tang Gan Urn, the Gainurn building served as one the founding stones for years to come.

Finally, in 1958, Tang bought a 1,351-square-metre piece of land at the corner of Orchard Road as part of his expansion plan.

Photo credit: RootsSG

Although the site faced the Tai San Ting Cemetery (See above!), he strongly felt that this land had much value as many British housewives could stop by as they continue on their journey into the city.

Despite disapproval from other fellow businessmen who felt that Orchard Road was unfashionable and unprofitable, Tang was firm on his decision and strongly believed in his own judgement.

This move was eventually acknowledged and credited to have been the spark that eventually transformed this dusty old road into what it is today.


Tang Plaza
Photo Credit:

With the newly acquired land plot, Tang constructed the now landmark C.K. Tang Department Store (later rebranded as Tangs) at 310 Orchard road with a sum of $50,000.

The building’s use of striking green-tiled roof and overall facade was greatly modelled after the Imperial Palace of the Forbidden City in Beijing, giving the mall a grand and majestic look to it.


Tang eventually retired in 1987 but reportedly never really kept his hands off his precious company, as he was often seen personally checking merchandises and goods, along with meeting several suppliers himself.

He eventually passed away in 2000, at the age of 98, in his home and surrounded by his loved ones.


Being a shopping district, many would be too distracted by all the different sights to see and goods to buy and unknowingly walk past some of the richest heritage and history to explore.

If you would love to bring your team or classes out for a fun day out to explore Singapore, feel free to check out our Customisable Learning Journey Tour! Do check out our previous article on the Sembawang Heritage Trail for its own route experience as you discover the prominence of Sembawang!

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