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The best historical trails in Singapore

Get learning and walking about Singapore's past at these historical trails around town

Photograph: Philippe Put/Flickr

History, we've got some. But you don't have to be stuck in a history class or a museum – get out there and explore history in the real world. It's time to explore landmarks and get to know the stories behind some of them. From the entire stretch of Bukit Timah to the significance of Fort Canning Park, get learning and get walking!

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Things to do

Fort Canning Park

City Hall

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. 

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Little India

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 race course, which became a focal point for this community. Durinf 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.

bukit timah

Bukit Timah

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 but be prepared to be walking and trekking – so wear some good walking shows

Fort Canning Park
Photo: Delfina Utomo

Civic District Tree Trail

A heritage trail on trees? Surprisingly, trees tell us more about history more than you know. The Civic District Tree Trail takes you through Singapore’s historic Civic District. Through the 3km trail, marvel at the beautifully conserved buildings along the way and also the majestic and interesting trees, some of which have stood tall for several generations and witnessed the transformation and progress of Singapore through the years.

TOUR with the National Parks Board as they take you through Raffles landing site and also to look and learn about some 130 year old trees.

Ann Siang Hill Park
Photo: Delfina Utomo

Telok Ayer and Ann Siang Hill

If you want to do a quick history trail, this 30-minute trek is fun one to check out. Beginning at Telok Ayer Street and ending at Club Street, the trail goes through Ann Siang Hill Park, a Chinese enclave stepped in history. 

Telok Ayer Street was the landing site for immigrants in the 1820s. Telok Ayer means "water bay" in Malay, as the area was only a few metres away from the original shoreline of the Singapore River. Upon landing, immigrants set up places of worship here to pray for safe journeys which is why you get your fair share of temples and shrines there. 

TOUR with National Parks Board and you will also discover that Ann Siang holds many botanical secrets as well like nutmeg, cinnamon, tamarind and breadfruit trees.



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 you will learn about Singapore's first satellite estate and see some pastel-coloured HDB blocks that still stand, as well as iconic landmarks that has defined the Queenstown over the years.

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

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