15 Fascinating Heritage Trails to Embark on with Your Little Ones



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Here are 15 fascinating heritage trails that will bring you and your little ones on an awe-inspiring ride through history!

Every day we’re rushing from one point to another to go to work, bring the kids to school, grocery shopping, and so on that we don’t realize the history that lies undisturbed in the building and roads we pass by. 

For example, most of us shop for Gucci bags and Christian Dior shoes at Orchard Road but we’ve never really thought about what it was before a shopper’s paradise. And what we’ve learned through textbooks and lectures, we’ve probably forgotten.

So why not take a walk down the timeline and explore the forgotten days of olden Singapore.

Last updated: 23 Jun 2021

1. Queenstown Heritage Trail

Queenstown Heritage Trail - Colonial Terraces

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Trail Points: 40

My Queenstown Heritage Trail recounts the story of Queenstown and visits the iconic landmarks which define the Queenstown skyline for the past 60 years. As the first satellite estate, the trail also tells you about the evolution of public housing in Singapore through personal stories of older residents.

Produced by My Community, with the support of the National Heritage Board, the Queenstown Heritage Trail has 40 trail points, including Alexandra Fire Station & Queenstown Neighbourhood Police Centre, Colonial Terraces at Jalan Hang Jebat, The First Flatted Factory, Black & White Bungalows and Former Malayan Railways. 

Writer's Note: If you feel there are too many trail points to cover in one day, you can always divide the places into two or more days to complete! 

2. Bedok Heritage Trail

Bedok Heritage Trail

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Trail Points: 10

From pirates to beach parties, fishing villages to coconut plantations, the story of the eastern coast of Singapore shares many common threads with coastal settlements across the world. At the same time, the intertwined histories of Bedok, Siglap, Tanah Merah and the East Coast are unique in many ways.

From the ancient days when Orang Laut fleets looked upon the red cliffs of Tanah Merah as a navigational guide, through the era of colonisation, all the way to Singapore's independence and present day, the area’s transformative journey is told through the branching stories of Bedok and the East Coast in this Bedok Heritage Trail. Your journey will bring you from Siglap Frankel Estate and Opera Estate to Military Landmarks in the East.

3. Bukit Timah Heritage Trail – Kampong Life Trail

3. Bukit Timah Heritage Trail – Kampong Life Trail - Railway

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Trail Points: 4

Buildings and institutions that were once part of Bukit Timah’s kampong past can still be found in the area today. The Bukit Timah Heritage Trail – Kampong Life Trail features a former railway station as well as houses of faith that were once central to the religious and social lives of kampong residents and now serve the same function for their respective congregations.

4. Bukit Timah Heritage Trail - WWII Legacy Trail

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Trail Points: 4

During World War II (WWII), Bukit Timah was a key target for the Japanese as the British supply depots, reservoirs and the strategic Bukit Timah Hill were all located in the area. The Bukit Timah Heritage Trail - WWII Legacy Trail explores WWII-related sites as well as places that carry the memories and legacies of the Japanese Occupation.

5. Tiong Bahru Heritage Trail

Tiong Bahru Heritage Trail - Graves of Tan Tock Seng-Chua Seng Neo-Wuing Neo

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Trail Points: 10

Tiong Bahru Road today stretches for more than three kilometres from Redhill MRT at its western end to Outram Road on its eastern end. For most Singaporeans, Tiong Bahru is a small, charming and chic housing estate awash with good eateries and eclectic little shops. But there is much more to Tiong Bahru than meets the eye. 

Did you know that Tiong Bahru Road was formerly named Burial Ground Road as it led from Outram Road into an area surrounded by numerous Chinese burial grounds? Embark on the Tiong Bahru Heritage Trail to discover the different facets of the estate. Your journey will bring you across the graves of Tan Tock Seng, Chua Seah Neo & Wuing Neo, the Seng Poh Garden & Dancing Girl Sculpture, and the Horse-shoe Block, among others.

6. Orchard Heritage Trail - Communities and Cemeteries 

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Trail Points: 14

The Orchard Road of today is filled with shopping centres, restaurants and entertainment outlets, but the Orchard Road of the past had a different character and was dotted with places of worship, schools, homes, community organisations and cemeteries. The Orchard Heritage Trail - Communities and Cemeteries route features residential and community sites of Orchard Road.

7. Jubilee Walk

Jubilee Walk - The Fullerton Waterboat House

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Trail Points: 24

Encompassing historic and iconic areas such as Fort Canning Hill, the Singapore River, the Civic District and Marina Bay, Jubilee Walk offers a chance to discover the people and communities who have contributed to our cityscape. The draw of Singapore as a 14th century regional trading hub, the vision and toil of both colonial and immigrant pioneers, and the fiery days of “Merdeka” (freedom or independence in Malay) are just some of the stories waiting to be told here, as are the experiences of modern-day Singapore overcoming the odds to become one of the leading global cities today.

8. Little Indian Heritage Trail – Serangoon in the 1900s

Little Indian Heritage Trail – Serangoon in the 1900s - Residences of Tan Teng Niah

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Trail Points: 11

The early 20th century was a defining period that shaped today's Little India as migrants from India, China and Britain settled in the area and established a diversity of trades and institutions. Follow this Little Indian Heritage Trail – Serangoon in the 1900s and explore the rich history of the Little India precinct.

9. World War 2 Heritage Trail

World War 2 Trail

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Trail Points: 20

The Second World War came to Malaya and Singapore on 8 December 1941, more than two years after it broke out in Europe. The war ended in the Asia-Pacific with the signing of the Instrument of Surrender in Singapore on 12 September 1945.

As part of the efforts to commemorate the 70th anniversary of the Fall of Singapore, the National Heritage Board launched a new World War II Trail in 2013. This contains information about the historic sites and events associated with the Battle for Singapore and the Japanese Occupation. It identifies war sites all over the island. Each site marks either a battle area, such as the invasion sites at Sarimbun beach, or commemorates a significant event during the Occupation, such as the Sook Ching massacre sites.

10. Balestier Heritage Trail – Faith, Film and Food

Balestier Heritage Trail – Faith, Film and Food - Goh Chor Tua Pek Kong Temple

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Trail Points: 11

The Balestier area is home to many places of worship, traditional food trades as well as landmarks from the Golden Age of Malay Cinema. This thematic trail brings you to religious buildings, a former movie studio as well as “makan places” around the neighbourhood.

11. Balestier Heritage Trail - Historical Landmarks of Balestier

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Trail Points: 10

Balestier Road is home to many historical sites, from colonial-stye villas to traditional shophouses and temples. The Balestier Heritage Trail - Historical Landmarks of Balestier will introduce you to some landmarks that have shaped Balestier Road from its early days to the recent past. Trail points include the Sun Yat Sen Nanyang Memorial Hall, Maha Sasanaramsi Burmese Buddhist Temple, and Balestier Market.

12. Hougang Heritage Trail - Landmarks of Hougang

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Trail Points: 9

Dive into the history of Hougang by visiting key landmarks along Upper Serangoon Road that have been associated with the area for more than 70 years with the Hougang Heritage Trail - Landmarks of Hougang. This trail takes you down one of Singapore’s oldest roads and introduces sites that represent the diverse communities who lived and worked in Hougang, such as the Church of the Nativity of the Blessed Virgin Mary, Former Simon Road Market and Hougang Tou Mu Kung. 

13. Geylang Serai Foot Trail

Trail Points: 13

This Geylang Serai Heritage Trail covers a large area, from Lorong 22 Geylang in the west to Geylang Serai in the east, and from Sims Avenue in the north to Guillemard Road in the south. The Trail lets you explore the various historical buildings and religious places of worship, including churches, temples & mosques, which represent the religious harmony that Singapore enjoys as a multi-racial, multi-cultural country.

14. Sepoy Lines Trail

Trail Points: 10

The Sepoy Lines area including Pearl's Hill and Outram has been a space of great significance in the early migration of Sikhs to Singapore and to the establishment of a settled community. This Sepoy Lines Trail by by Mr. Ishvinder Singh features the Former Outram Prison, The Lower Barracks, Former Gurdwara Pearl's Hill, and Silat Road Sikh Temple, among others. 

15. Singapore Maritime Trail

Trail Points: 2

The Maritime and Port Authority of Singapore’s Singapore Maritime Trails are designed to help raise the awareness of Maritime Singapore. The trails tell the story of the development of Singapore’s maritime industry through a tour of selected locations and the first trail focuses on Singapore’s Maritime Heritage.

Image Source: National Heritage Board


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This article is prepared by

Malini Pannirselvam
Dedicated writer by day, avid reader by night, language fanatic all the time, and aunt to nieces and nephews every day

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