Exploring the rich history of Singapore's Orchard Road via walking tours

Beyond the upscale boutiques and Michelin-starred restaurants, historic sites and green spaces tell the real story of this popular precinct

Winsland House II is one of several elegant colonial buildings along Orchard Road. Photo: Ronan O'Connell

Like an Asian version of Paris’s Champs Elysees or New York’s Fifth Avenue, Singapore’s Orchard Road is one of the continent’s most famous retail and dining precincts. It is so laden with luxury boutiques, Michelin-starred restaurants and plush hotels that tourists could spend an entire Singapore holiday on this 2.2km thoroughfare.

But, as they wander through this neighbourhood, observant travellers will also notice a number of historic locations that illustrate how Orchard Road wasn’t always a luxury hub. They can also follow the Orchard Heritage Trail, which guides tourists through 28 sites that tell the remarkable tale of how Orchard Road was transformed from a farming village into a beacon of decadence.

Singapore is one of the world’s most modern cities and many tourists are drawn by its cutting-edge attractions — from the towering Marina Bay Sands to the space-age Gardens by the Bay. Yet, embedded in these skyscraper-spiked surrounds is a trove of engrossing history.

The Singaporean government has recently poured resources into showcasing the little-known back stories of its tourist districts, including Orchard Road. To do so, its National Heritage Board has crafted more than 20 walking trails, each listed on its website, with route maps and detailed histories.

These marked walking routes variously highlight how Singapore was besieged by pirates, tackled endemic corruption, survived a Japanese invasion and created a tourist attraction at a place called “death island”. I followed four routes, as well as the Orchard Road trail, on my last visit.

While walking the Bedok Trail, I learnt that Singapore has been dealing with an ocean crime scourge for 500 years. In 2021, the Singapore Strait ocean passage was a hotspot of piracy, with 46 incidents, more than in the rest of Asia combined. Few tourists will know that pirates have operated in Singapore’s seas since the 1500s. Or that their bloody crimes are a reason Singapore’s Sentosa Island, now a popular holiday spot due to its theme parks and clean beaches, was previously known as Pulau Blakang Mati, which translates as “the island behind which lies death”.

This riveting story is highlighted by the Sentosa Heritage Trail, which I followed past 15 locations on the island, including Fort Siloso, a large hilltop fort that played a key role during the Second World War, when Singapore was invaded by Japan. Tourists can delve further into this event as they walk the World War II Heritage Trail, which passes directly by Orchard Road.

The Orchard Heritage Trail begins at Dhoby Ghaut Green, at the eastern end of Orchard Road. Many tourists pass this open space each day on their way to or from nearby attractions such as the National Museum of Singapore, Plaza Singapura shopping centre or ancient Fort Canning.

This end of Orchard Road is home to two important structures, each marked on the trail. The YMCA is Singapore’s first community centre, while the Orchard Road Presbyterian Church is a graceful, whitewashed, neoclassical building that’s among Singapore’s oldest churches, dating back to the 1870s.

From there, I walked west to Istana Park. Located on Orchard Road, this is a small but attractive green lung, embellished by a colourful array of orchids, Singapore’s national flower. I couldn’t miss one of the trail’s locations, the unique cream-and-red SMA House, a century-old building topped by an odd, scallop-shaped arch.

Here I learnt that, in the late 1800s, Dhoby Ghaut was a buzzing market for horse carriages. Then, in the early 1900s, it became a hub for the sale of motorcars, with a huge vehicle showroom located in SMA House. And before all that, about 200 years ago, Dhoby Ghaut was a rural area.

At that time, Singapore’s centre was near the mouth of the Singapore River, an area now studded with tourist attractions such as the Merlion statue, Marina Bay Sands, the Asian Civilisations Museum and leafy Esplanade Park. That area was chosen for development by the British, who in 1819 created a settlement that was the cradle of modern Singapore.

Dhoby Ghaut, back then, was home to a garrison of Indian soldiers employed by the British. They would wash their clothes in Orchard Road’s stream, which earned the area its name — in Hindi dhobi refers to washerman, while ghat means a riverside location for bathing or doing laundry.

I found no sign of that waterway as I continued west to another trail marker, the beautiful Penang Road Open Space, which hosts more than a dozen butterfly species. Or when I visited the nearby House of Tan Yeok Nee. With its complex mosaics, decorative eaves, steep ceramic roof and peaceful courtyards, this majestic mansion was built for a wealthy Chinese merchant in the 1880s.

Back then, Orchard Road was cloaked in pepper plantations and fruit plantations. There was also a large nutmeg farm in what is now one of Singapore’s most picturesque old neighbourhoods, Emerald Hill. This was where I finished my walking tour of Orchard Road’s past.

Emerald Hill’s elegant shophouses, painted in a wide palette of colours and decorated with flowers and birds, contrasted starkly with the gleaming skyscrapers that loomed above. This area hides just to the north of Orchard Road, down narrow side streets. Tourists could easily miss it, unless they take the time to take in one of Singapore’s terrific heritage trails.