Celebrate Singapore's jubilee by rediscovering the island’s icons that tell the story of its rise from fishing village to world-class city
Celebrate Singapore’s jubilee by rediscovering the island’s icons that tell the story of its rise from fishing village to world-class city
Photo credit: Athena Tan

It is the year of Singapore’s jubilee - 50 years of development and transformation. Born and bred in Singapore, I cannot help but feel a sense of excitement and pride. In honour of SG50, I have designed three special trails to help you discover the Singapore I love. So, pack your bags, book yourself a staycation at our Ascott serviced residences and join me. Your journey through the best of the country is about to begin.

Trail One: Raffles Trail

Starting point:Ascott Raffles Place Singapore

What is it:This trail will take you through some sites that feature in the modern history of Singapore which began in 1819 when Sir Stamford Raffles made this fishing village a British port.

Ascott Raffles Place Singapore is a heritage building in itself and so a fitting start for our History Trail. The 1950s Art Deco inspired architectural icon, once the tallest building in the country, still has many of its original design features.

Cross the street to Collyer Quay where you will see Clifford Pier . No longer in use, this was the landing point of migrants when they first came to Singapore hoping to improve their fortunes.

Continue walking with your back to Ascott Raffles Place Singapore. To your left is Raffles Place (formerly known as Commercial Square), Singapore’s first commercial centre. Then, as it is now, the area was a business district. In the latter half of the 19 th century, it was also a premier shopping hub. Robinson department store (which you can visit further down the road at Raffles City Singapore), first opened its doors here in 1858.

Within 10 minutes, you will come to the Merlion – the lion-headed-fish-tailed statue that spouts water when the tide is high. The 8.6-metre tall symbol of Singapore’s start as a fishing village named Singapura (Lion City) by Prince Sang Nila Utama when he discovered it in the 11 th century sits guarding the mouth of Singapore River with its two-metre tall cub.

Across the road is Cavenagh Bridge, the only suspension bridge and one of the oldest bridges in Singapore. It was built in 1869 to allow people to cross the Singapore River. To its right is its cousin, Anderson Bridge,built in 1909 to replace Cavenagh Bridge when it could no longer accommodate the high traffic.

Walk along the Singapore Riverand you will come to the spot where Sir Stamford Rafflesfirst landed in Singapore on 29 January 1819. His statue stands as a reminder of the city’s colonial past. I love the river because of its sense of history.

Another 10 minutes or so up river and you will reach your final stop – Clarke Quay . The dining and partying hub was once the centre of Singapore’s trading activities. The warehouses that used to store goods have all been converted into trendy watering holes and restaurants but the colourful façade continues to bear witness to the site’s past. Rest here and have your pick of any number of cafés and restaurants and marvel at how far Singapore has come.

Trail Two: World War II Trail

Starting point:Somerset Liang Court Singapore

What is it:Relive this slice of history as you visit some of the places where World War II ensued in Singapore.

Somerset Liang Court Singapore is a 197-unit serviced residence that is right across the street from Fort Canning Parkand, therefore, the most convenient place to begin your World War II trail. I would know because my family and I once had a staycation at the serviced residence and did just that.

Put on your hiking shoes and scale Fort Canning Hill, once the seat of the Malay Kingdom, Temasek, and the burial ground of the Sultans. This is also where Sir Stamford Raffles built his residence, the first Government house.

The hill would again feature in World War II when Lieutenant-GeneralA E Percival established his command post of the Malayan Command at the fort in February 1942 in his failed bid to hold off the invading Japanese forces. The Japanese later took over the fort for its military uses.

Descend the other side of Fort Canning Hill to get to the Cathay Building . Before the war, it was the headquarters of the Special Operations Executive Orient Mission which trained guerillas to infiltrate Malaya. As the Japanese attack escalated, the British would try to spot military guns from the roof of the building. When the British surrendered, it became the Japanese Propaganda Department Headquarters from which messages from the Japanese government were broadcasted.

Across the street is a YMCAthat served as the Kempeitai (Japanese Military Police) East District Branch. Here, suspected anti-Japanese locals were imprisoned and tortured for information.

Return to modern Singapore at Plaza Singapura located a two-minute walk away at Dhoby Ghaut. Until the early 1900s, the Dhobis (who washed clothes for a living) used the water from the Sungei Bras Basah (now Stamford Canal) to do their laundry, lending the area its name. Plaza Singapura was once one of Singapore’s largest malls in the 1970s. It is one of my favourite malls because here, you can rest your feet and have a bite at any number of restaurants, cafés and food kiosks in the mall.

Trail Three: Built to Last Trail

Starting point:Somerset Orchard Singapore

What is it:Buildings tell a story, too. This trail takes you to different buildings in Singapore whose architectural beauty and historical importance map out the country’s story.

Located just off the main shopping thoroughfare of Orchard Road is the 88-unit Somerset Orchard Singapore which offers home-style comforts in the midst of the bustling city. From there, walk less than 10 minutes and you are at Emerald Hill, once a Peranakan enclave. Stroll amongst the Peranakan-style homes and shops, and soak in the old-town atmosphere.

Somerset MRT station is across the street from Emerald Hill. Take a train up three stops to City Hall station and emerge from the station at St Andrew’s Cathedral . Built in 1861, Singapore’s largest cathedral boasts a Neo-Gothic architectural style inspired by Netley Abbey, a ruined 13 th century church in Hampshire, England.

From here on, it is building after building whose gorgeous architecture speaks of a glorious era in its past. Walking away from the church, with the green expanse of The Padang to your left, head towards the City Halland old Supreme Courtadjacent to it. The City Hall, completed in 1929 and gazetted as a national monument in 1992, has borne witness to many historical events. The surrender of the Japanese in September 1945; then Prime Minister, Lee Kuan Yew’s declaration of self-rule in 1959; the merger with Malaysia in 1963 and the swearing in of Singapore’s first fully-independent government in 1965 all took place within its halls.

Together with the old Supreme Court, the last structure in Singapore built in the Classical style by the British, the buildings are impressive testimonies to the architecture of their times with their Corinthian columns and interior murals.

Just 200 metres away is the Old Parliament House, the oldest government building still standing. Built in 1827 as a private residence and spotting colonial influences in its design, it is today The Arts House. Look out for a bronze elephant statue that welcomes all who enter, a gift to Singapore from King Chulalongkorn of Siam.

Next door is the Victoria Theatre and Concert Hall . The former Town Hall in colonial times is another gazetted national monument. Comprising two buildings and a clock tower, its façade shows off the Palladian architectural style that gives the structure coherence.

The last stop in this trail is 10 minutes away. The Central Fire Stationturned 100 in 2009 and was nicknamed ‘Blood and Bandage” building in reference to its candy stripe red and white exterior. The oldest fire station in the country, it also houses a heritage gallery that traces the Civil Defence’s progress. You can view antique fire engines and firefighting equipment at the gallery or take a tour up the station’s hose tower, Singapore’s highest point in the 1920s.

Walking through these trails is a vivid reminder that this vibrant city forging ahead to establish a hopeful future for its people is a nation built on the visions, efforts and successes of its past. As we look forward on this 50 th year of nation building, let us remember the roots from where we came. Have fun, Trailblazers!

Stay with us:

Ascott Raffles Place Singapore

Citadines Mount Sophia Singapore

Somerset Bencoolen Singapore

Somerset Liang Court Singapore

Somerset Orchard Singapore