The best historical trails in Singapore

The Singapore River has served as an artery of international commerce that drew people from all over the region to work, trade, and seek their fortunes on this island even before its modern development. Today, the river continues to bustle with life, flowing past modern skyscrapers and historic buildings, and under bridges with interesting stories – think the oldest bridge in Singapore (Cavenagh Bridge), the bridge with a morbid past (Anderson Bridge), and the colourful bridge (Alkaff Bridge). There are also life-like sculptures along the river bank for a glimpse of life by the river in Old Singapore.

TOUR with Singapore River Walk by the National Heritage Board. It's a virtual tour that traces the development of the river spanning from Collyer Quay to Robertson Quay. Learn about the contributions of the river towards Singapore’s mercantile development through the various communities who lived and worked by the river, as well as the spectacular architecture and social history of the bridges that criss-cross the river facilitating the movement of people and goods across the river at various junctures.

Explore the many nooks and crannies of Fort Canning Park and its many colonial-era relics, learn more about the paramount roles it played in the defence of the island during the times of war and even before the British arrived when it served as the residence of Malay royalty.

TOUR with guided tours by Battlebox, the former WWII British underground command centre which was part of the headquarters of Malaya Command, the army which defended Malaya and Singapore in WWII – so you know there's a lot of history to be learned. It was inside the Battlebox that the British made the decision to surrender Singapore to the invading Japanese on 15 February 1942.

Designated as a national monument in 2006, the first auto assembly plant in Southeast Asia was also the place where British Forces surrendered Singapore to the Japanese army in 1942. It’s now a museum which, through pictorial exhibits and film documentaries, details just how residents in Singapore and Malaya lived during the Japanese Occupation.

TOUR the Former Ford Factory. Alternatively, you can navigate the events and memories via its immersive, 360-degree virtual experience. Expect oral history accounts, archival records, and published materials.

History buffs will enjoy a wander around this World War II-related site. Fort Siloso tells the story of Japan’s victory through punchy displays on resistance hero Lim Bo Seng and Force 136, and of the local civilian experience during the Japanese occupation. The main attraction is the sprawling structure of the fort itself, complete with coastal guns, winding tunnels, and a treetop trail.

TOUR the Surrender Chambers which has exact waxwork replicas of the main players, and is surprisingly effective at reconstructing the British surrender to the Japanese, and vice versa. There are also tunnels where you can examine original guns, cannons, film clips, and photographs from days past. Real danger not included.

It's not just about the attention-grabbing aesthetics of the shophouses – Chinatown is peppered with features that shed a light on its bustling past. The sculptures of Samsui women, rickshaw pullers, and coolies resting after a hard day's work offers a glimpse of its rich history.

TOUR the Chinatown Heritage Centre if you're willing to dig further. While it remains temporarily closed, for now, the building itself stands as a proud reminder of Chinatown's storied past. Inside, the revamped centre features a replica of a tailor shop, sundry store, and crowded living quarters spread across three storeys of a shophouse – common sights in Old Singapore. Heightening the experience are ambient soundscapes and audio conversations that evoke the buzz of those bygone days. Its reopening will be announced on its Facebook page at a later date.

Don't be fooled by its name – Kampong Glam isn’t all that glamorous but it is one of Singapore's oldest (and hippest) neighbourhoods. Named after the Gelam tree, Kampong Glam was once home to the Malay royals in Singapore prior to the colonisation by the British in 1819. It then became an ethnic enclave for the Muslim community under the Raffles Plan of 1822. Now, it’s a melting pot of vibrant cultures, rich history, eye-popping street art, charming restaurants, and trendy shops.

TOUR the Malay Heritage Centre which is located at the historic Istana Kampong Gelam, once the royal seat of Singapore’s sultans. The museum traces the rich history of the Malay community from the days of its earliest settlers and the sea-faring might of the Bugis villagers to the golden years of the Malay entertainment industry.

Little India is the heart of Singapore’s Indian community and is also an area rich with stories and history. Originally named Serangoon, what is now known as Serangoon Road was laid out by Indian labourers and convicts. In the early 1840s, Little India thrived as a residential enclave for the Europeans following the completion of the racecourse, which became a focal point for this community. During this time, cattle trading in Little India began to blossom due to its location along the Serangoon River, paving the way for Little India to be the bustling commercial area it is today.

TOUR with the Indian Heritage Centre as you cover over 40 heritage sites across four kilometres. Choose from three specially curated thematic routes that bring you across the precinct’s historical landmarks, places of worship and retail offerings.

The official Bukit Timah Heritage Trail first started in 2007 and has been refreshed by the National Heritage Board recently to include new places of interest, and even oral histories from people in the community. Choose between three thematic trail routes, history buffs, and go on the WWII history-centric trail while those curious about the residential neighbourhood in the past, there is one with a focus on the kampong life back in the days.

TOUR with National Heritage Board's revamped Bukit Timah tour which is free and easy, so you can plan it out on your own. But be prepared to be walking and trekking – so wear some good walking shoes.

There are many things to learn about this 60-year-old estate in Singapore. Named after Queen Elizabeth II to mark her coronation and created to tackle the overcrowding problems in Chinatown. The heritage trail schools you on Singapore's first satellite estate and the pastel-coloured HDB blocks that still stand, as well as iconic landmarks that have defined Queenstown over the years.

TOUR with Roots.sg where you can embark on this personalised tour and see the sights at your own time. 

This sleepy, northern coastal town has more than you'd expect in terms of history. The new Sembawang Heritage Trail by the National Heritage Board will regale you with the area's rich naval history and the stories of the diverse communities that used to live and work here. Visit up to 31 sites on the trail, including the former Sembawang shipyard, the Sembawang strip, and the stately Beaulieu House and jetty. Learn also about what used to be: rubber plantations that covered the land and coastal kampongs by the sea.

TOUR The Sembawang Heritage Trail e-guide and trail map are available on Roots.sg. With these in hand, embark on one of three distinct routes and read up on a wealth of information about the area's history and sites of interest.