5 historic roads in Singapore and the stories behind them

Constructed between 1833 and 1835, North Bridge Road is one of the oldest roads in Singapore. Running from Crawfurd Road to Elgin Bridge where it merges with South Bridge Road, this major road used to be a one-way street lined with as many as five movie theatres and bustling with trams and trolley buses. The nearby Hill Street has an interesting history too – it was the very first street laid out in Singapore and was a popular shopping destination for the elite in search of imported European textiles and tailoring services offered by Sindhi and Sikh merchants. 

GO Shop at Funan Mall for the latest in electronics, or Bugis Junction for lifestyle and apparel. Visit CHIJMES for trendy restaurants and bars, or the National Library for quiet reading time. 

Bukit Timah Road stretches 25 kilometres from the city centre to Woodlands Road, making it one of the longest roads in Singapore. Though it's known to be lined with expensive landed houses today, the land around Bukit Timah Road used to be covered with gambier and pepper plantations – and infested with tigers. 200 people were killed in 1860 alone, so it wasn't the safest of places to live. And weird fact: apparently Bukit Timah Road was the site of the first horseback ride in 1840. A Mr. Thomson and Dr. Little took four days travelling down this road on the backs of their four-legged companions.

GO Hit up The Grandstand for some delicious fare, including Thai food at E-Sarn or beers and bites at Kult Kafe (relocated from Emily Hill). This is also the road to get on to access some of the best natural landmarks in Singapore, including Bukit Timah Nature Reserve and Singapore Botanic Gardens. 

This charming road in the east used to hug the southeastern coastline of Singapore, and was a popular place for the rich to build bungalows by the sea. Major land reclamation put that to rest, but East Coast Road is no less idyllic. Demarcated in 1828 in Lt. Philip Jackson's Town Plan, this road (along with West Coast Road) is among the earliest delineated roads in Singapore although it was only built in 1902. It is highly associated with the Peranakans and Eurasians, ties that have lasted till today.

GO Visit the Katong Antique Museum for a taste of Peranakan history and culture. And it would be a crime to miss out on some of the best laksa that Singapore has to offer – you can find a few options clustered near Roxy Square. 

Bras Basah, meaning 'wet rice' in Malay, used to receive boats heaving with tons of rice that were laid down on the banks of the river to dry. Unfortunately, it seems that high tides would get the grains wet anyway. That's said to be the origin of the name of Bras Basah Road, a present-day art and cultural district. Nearby Waterloo Street and Queen Street are one of the oldest streets in Singapore too. The former is lined with religious buildings that speak to Singapore's multicultural community; the latter has a strong Eurasian presence and was known for the many churches along it, including our oldest Roman Catholic church, called the Cathedral of the Good Shepherd. 

GO Book lovers and craftsmen can head to Bras Basah Complex for secondhand books and art supplies. Basheer Graphic Books is a favourite of ours. In the vicinity are arts institutions like Nanyang Academy of Fine Arts, Esplanade and the National Museum of Singapore. 

There are two theories about where the name Mandai Road came from. Some say it was named after an unidentified tree, while others believe that it comes from the Malay word mandi, meaning 'bathe', referring to the river R.Mandi as labelled in early plans of Singapore. Today, most people head along Mandai Road to get to the Singapore Zoo, but it's kind of a hotspot for our national flower too. The Mandai Orchid Garden is a 4-hectare, privately-owned garden; nearby, Orchidville private orchid farm stands as the largest orchid farm in Singapore, covering over 43 hectares of land. Travelling along the road, you also won't miss its lushness, so you'll be glad to know that it's been recognised as a Heritage Road and assigned conservation status. This means that the mature trees and plants within a 10-metre buffer zone cannot be cleared or realigned unless under very special circumstances.

GO To Mandai Zoo! There's also the Night Safari, River Safari and Bird Paradise. In the future, we can also look forward to the new Rainforest Park.