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Best Heritage Trails in Singapore That History Buffs Swear By

Best Heritage Trails in Singapore That History Buffs Swear By

As a history enthusiast, nothing brings me more pride as a Singaporean than when a tourist shows genuine interest in my impromptu stories about Singapore’s rich history and iconic landmarks.

If you’re a history buff like me, I compiled a list of the top heritage trails in Singapore you can use to explore and discover the island’s best landmarks. 

No need to fret. These tours are all self-guided, so you won’t have me talking your ears off!

Heritage Trails from the National Heritage Board

Orchard Road Historical Gems Heritage Trail 

Starting Point: Royal Thai Embassy, 370 Orchard Rd

Ending Point: Emerald Hill Conservation Area, Emerald Hill Rd

Trail Duration: Around 40 minutes 

Trail Length: Around 2.2 kilometres


One of my favourite heritage trails in Singapore is actually located right at the heart of the island’s central business district. Orchard Road may be known to many as a shopping destination, but it’s also a treasure trove of historical landmarks. 

This trail, in particular, will take you through Orchard Road’s most iconic historical landmarks (with a heritage spanning 200 years), starting at the Royal Thai Embassy and then ending at Emerald Hill. 

Some important sites to see along this trail are Tang Plaza, Orchard’s oldest department store, The Mandarin Oriental, Singapore’s tallest structure in the 1970s, The Hereen, a 1930s hallmark of Peranakan heritage in Orchard, and more. 


Sites like the Royal Thai Embassy and the former Singapore Chinese Girls’ School are not open to the public. You’ll be seeing these sites along the trail but only from the outside. 

You have the option to take the bus from Goodwood Park Hotel to the Mandarin Oriental Hotel to shorten the trail’s duration by 10 minutes! (This will also help you beat the heat if you’re doing the trail during the day).

Toa Payoh Of Faiths & Beliefs Heritage Trail 

Starting Point: Lian Shan Shuang Lin Monastery, 184 Jalan Toa Payoh

Ending Point: The Tree Shrine, 177 Toa Payoh Central

Trail Duration: Around 2 hours

Trail Length: Around 6 kilometres


Another heritage trail I highly recommend is the Of Faiths & Beliefs Toa Payoh Heritage Trail. There are a total of 8 points of interest along the trail, all of them being places of worship for the diverse communities residing in Toa Payoh. 

This trail highlights the district’s religious significance to the many ethnic communities present there. It’ll take you about 2 hours to complete the whole 6-kilometre trail on foot and by bus. 

Some important sites include the Lian Shan Shuang Lin Monastery, the Tree Shine, the Toa Payoh Methodist Church, the Sri Vairavimada Kaliamman Temple, the United Five Temples of Toa Payoh, the Seu Teck Sean Tong, and the Masjid Muhajirin.


Since you’ll be visiting sacred places of worship, I suggest wearing modest but comfortable clothing when embarking on this trail. Keep your shoulders and knees covered, and if possible, bring a light jacket or cardigan with you. 

You don’t have to enter the temples along the trail if you don’t want to. You can take pictures from the outside instead (especially if there are masses, services, or prayers happening during your visit). 

Changi Heritage Trail

Starting Point: Changi Cottage, 26 Netheravon Rd

Ending Point: Singapore Changi Airport, 60 Airport Blvd. or Singapore Navy Museum, 112 Tanah Merah Coast Rd

Trail Duration: Around 3 hours

Trail Length: Around 16 kilometres


The Changi Heritage Trail is one of the longer trails on this list, but it is a rewarding one because of the important sites you’ll encounter along the way. There are a total of 15 points of interest in the trail, many of them located by the coast of Changi Beach. 

The trail along Changi Beach takes you through the heritage bungalows, clubs, and beach resorts that line the coast. Many of these structures were built between the 1920s and 1950s, and all represent Changi’s history as a leisure destination since the 1800s.

The rest of the trail takes you through the Changi Prison, the former Changi Hospital, Changi Point Ferry Terminal, Changi Village, and of course, Singapore Changi Airport. You also have the option to extend the trail and visit the Singapore Navy Museum! 


The Changi Cottage, one of the historic colonial bungalows located along Changi Beach, is only open to guests who have booked the entire venue for events. 

Moreover, you can’t really tour the interiors of these structures, but you’re free to visit the cafes and restaurants inside Changi Sailing Club and Changi Beach Club. 

Kampong Glam Heritage Trail 

Starting Point: 85 Sultan Gate

Ending Point: Masjid Hajjah Fatimah, 4001 Beach Rd

Trail Duration: Around 1 hour and 30 minutes

Trail Length: Around 2 to 4 kilometres


There are many ways to explore the Kampong Glam Heritage Trail, which is why this is one of the most family-friendly trails on this list. You’ll basically be exploring a whole neighbourhood with sites within walking distance from each other. 

Kampong Glam is one of the island’s most vibrant districts thanks to its lively art scene, with Haji Lane being the most popular hotspot in the area. The trail covers all the important sites like the Masjid Sultan and the Malay Heritage Centre. 

Other colourful lanes in this trail are Bali Lane, Arab Street, Bussorah Street, and North Bridge Road. These lanes connect you to every corner of Kampong Glam, with access to food stalls, restaurants, bars, and shops selling Malay fare and traditional textiles. 


There is no set path to explore the Kampong Glam Heritage Trail, but my recommendation is to start from the Malay Heritage Centre and then walk down along Haji Lane. 

Make a left then head towards the Masjid Sultan. From there, make another left to Muscat Street. 

Don’t miss your chance to buy handcrafted perfumes, traditional batik clothing, and belts while exploring Kampong Glam! 

Hougang Architectural Gems Heritage Trail 

Starting Point: Ramakrishna Mission, 179 Bartley Rd

Ending Point: Rainbow Block, 316 Hougang Ave 7, Block 316 or Chee Tong Temple, 62 Hougang Ave 3

Trail Duration: Around 1 hour and 45 minutes 

Trail Length: Around 4 to 6 kilometres


Hougang is where you can find some of the oldest existing roads in Singapore, with the most iconic one named Upper Serangoon Road. The Architectural Gems Heritage Trail takes you around the district’s famed landmarks dating back 70 years. 

This trail is one part of a three-part heritage series of Hougang, and it’s my favourite among them. There are a total of 8 points of interest, starting at the Ramakrishna Mission, a conserved temple built in the 1950s, and ending at the Rainbow Block. 

The Rainbow Block is a must-visit mural that depicts a colourful rainbow across Block 316. It’s become so popular among visitors and locals that no matter how many times it has been redesigned, the mural will always show a rainbow. 


If you don’t want to end the trail at the Rainbow Block, you have the option to extend it by visiting Chee Tong Temple. You’ll need to walk along Hougang Avenue 3 to reach it, which is just a short walk from the Rainbow Block. 

Take a short break from the trail after the Rainbow Block by heading towards Hougang neighbourhood Park from Hougang Avenue 7. 

There are benches, playgrounds, and a chicken petting corner to keep you or your kids occupied while you catch your breath. 

Ang Mo Kio Iconic Landmarks Heritage Trail 

Starting Point: Ang Mo Kio Town Centre, 720 Ang Mo Kio Ave 6

Ending Point: Dragon Playground, 570 Ang Mo Kio Ave 3

Trail Duration: Around 1 hour and 30 minutes 

Trail Length: Around 5.5 kilometres


When it comes to reliving childhood memories, I always think about Ang Mo Kio. From the iconic Dragon Playground to the Kebun Baru Bird Singing Club, this heritage trail will show you some of the very best examples of Singaporean life through the years. 

The trail starts off at Ang Mo Kio Town Centre, a popular lifestyle and shopping complex built in the 1970s, and ends at the Dragon Playground, an iconic dragon-shaped mosaic playground that has served hundreds of children since its opening in 1979. 

Safe to say, this is a heritage trail made for my parents who grew up in this neighbourhood. My other top pit stops along this route are Ang Mo Kio Town Gardens, Bishan-Ang Mo Kio Park, and the Bird Singing Club for a breath of fresh air in the city. 


Currently, the Dragon Playground is temporarily closed for maintenance, but you’re free to take pictures or catch sight of it before you end the trail. 

If you’re feeling famished, head over to The Pine Garden along Ang Mo Kio Avenue 10 to get yourself freshly baked goods. 

The bakery has been in operation since 1984 and is known for its pandan chiffon cake (a Singaporean delicacy). 

Tampines Town Heritage Trail 

– From wheretodapao

Starting Point: Our Tampines Gallery at the Tampines Regional Library, Lobby H, 1 Tampines Walk, #02-01 Our Tampines Hub

Ending Point: Tampines Round Market and Food Centre, 137 Tampines St. 11

Trail Duration: Around 1 hour and 30 minutes 

Trail Length: Around 4.7 kilometres


Tampines Town, awarded the World Habitat Award in 1991, is renowned as one of Singapore’s most innovative estate districts. I lived there before relocating to near Orchard a few years back and am proud to have been a resident.

The Tampines Town Heritage Trail doesn’t contain historical landmarks but instead features parks and sites that best demonstrate the town’s community spirit, housing innovation, food scene, and overall pulse. 

It starts at the Our Tampines Gallery where you can find a library and community centre, then ends at the Tampines Round Market and Food Centre. In between, you’ll be visiting the Tampines Central Park and the Tampines Chinese Temple! 


The best time to do the Tampines Town Heritage Trail is in the morning. 

Since your last stop is at the Tampines Round Market and Food Centre, I recommend finishing the trail by lunchtime because many stalls inside the food centre close by 3:00 pm. 

Our Tampines Hub is a large community centre that welcomes visitors for cultural events, workshops, and other activities. There’s Wi-Fi inside, so you can catch your breath or update all your followers about the heritage trail here. 

The Tampines Regional Library is open to all guests. I recommend cooling off in the library (great air conditioning) and browsing the collections here before setting off to complete the trail!

Bukit Timah Kampong Life Trail Heritage Trail 

– From nea_sg

Starting Point: Bukit Timah Railway Station, #1 Railway Station, Bukit Timah Railway Station Community Node

Ending Point: Fuyong Estate, Jalan Asas

Trail Duration: Around 1 hour 

Trail Length: Around 3 kilometres


If you’ve traversed through the Rail Corridor before, then some sites along the Bukit Timah Kampong Life Heritage Trail will be very familiar. The trail highlights Bukit Timah’s past of housing the railway connecting Singapore to the Malay Peninsula in the 1930s. 

That said, I recommend starting this trail at the former Bukit Timah Railway Station located along the Rail Corridor. From the railway station, make your way eastwards to Bukit Timah Road, then make a left down Sixth Ave. 

Once you reach the end, make a right down Jalan Haji Alias to reach Masjid Al-Huda, the central mosque of the Muslim community residing in Bukit Timah. The last stop (just down the street) is Hoon San Temple, a Chinese temple built by immigrants in 1902. 


Don’t just walk past the Masjid Al-Huda. There’s a heritage gallery where you can visit to learn more about the Muslim community life and history of the mosque in Bukit Timah. 

Extend your tour through this heritage trail by detouring down the Rail Corridor and visiting the Fuyong Estate, a housing estate built by Lee Kong Chian in the 1950s as a solution to the island’s housing shortage during that time. 

Afterwards, make your way down further the Rail Corridor, then cross the Upper Bukit Timah truss bridge, or head to the Rail Mall to refuel your energy with drinks and food. 

Sentosa Forts Heritage Trail 

Starting Point: Fort Siloso Skywalk, Siloso Rd

Ending Point: Fort Serapong, 54 Lakeshore View

Trail Duration: Around 2 hours 

Trail Length: Around 4 kilometres


Beyond its reputation for resorts, beaches, and theme parks, Sentosa is a treasure trove of historical sites. If you’re into that, the Sentosa Forts Heritage Trail takes you through Singapore’s best-preserved colonial forts dating back to the late 1800s! 

When I do this trail, I like to start from Fort Siloso Skywalk to take in coastal views of Keppel Harbour and the sea from the tower. This is best done in the morning as the sun rises, but you can also conclude the trail from here if you prefer sunset views! 

Along the route, you’ll pass by Fort Siloso, Pulau Blakang Mati, Siloso Pier, the Imbiah Battery, and then lastly, Fort Serapong. You can reach the peak of Mount Serapong from there and get sweeping views of all the colonial artillery batteries up there! 


Please take note that some areas surrounding the forts, particularly Fort Serapong, are closed off to the public. There are signboards and info guides scattered around Fort Serapong to keep you right on track in case you get lost! 

But seriously, just don’t venture off the road and head straight into the forests.

Another way you can reach Sentosa’s Siloso Point Station (where Fort Siloso Skywalk is located) is by cable car from Mount Faber or Harbourfront Station. 

This may add more minutes to the overall duration of the trail, but you’ll get extra awesome views to kick off the tour! 

Otherwise, take Sentosa buses A and C from the VivoCity Shuttle Bus Stop and alight at Siloso Point Station. 

Historical Landmarks of Sembawang Heritage Trail 

Starting Point: Holy Tree Sri Balasubramaniar Temple, 10 Yishun Industrial Park A or Sembawang Strip, 1018 Sembawang Rd

Ending Point: Sembawang Hot Spring Park, Along Gambas Ave

Trail Duration: Around 2 hours 

Trail Length: Around 7 kilometres


Did you know that Singapore’s Sembawang was inhabited by the Orang Seletar, a group of nomadic boat-dwelling sea people before the town became a major British naval base in the 1920s? 

Even today, Sembawang maintains its deep connections to its naval base heritage and the sea. The Historical Landmarks of Sembawang Heritage Trail lets you explore the significant landmarks that showcase this enduring legacy. 

Sites include the Former Admiralty House, the Sembawang Shipyard, the Sembawang Strip, the Sembawang Shopping Centre, the colonial houses of British naval officers, and lastly, Sembawang Hot Spring Park (Singapore’s only natural hot spring!). 


You can start this trail by taking a bus from Canberra MRT Station to Durban Road. Cross the road and head straight to the shophouses located along Sembawang Road. 

There’s actually another important site you can visit before heading to the Sembawang Strip: The Holy Tree Sri Balasubramaniar Temple, a Hindu temple originally built by Hindus working at the naval base. 

The original temple was first built in 1962 and then was relocated to its present site near Canberra Road. 

Don’t miss your chance to soak your tired feet in the natural hot spring at Sembawang Hot Spring Park! 

Fort Canning Park’s Colonial History Walking Trail 

Starting Point: Cox Terrace Roundabout, 51 Canning Rise

Ending Point: Raffles House, Fort Canning Park

Trail Duration: Around 45 minutes 

Trail Length: Around 2 kilometres


Calling all history buffs! The Colonial History Walking Trail at Fort Canning Park is my go-to for friends looking for heritage trails in Singapore that are packed with war mementoes, colonial forts, and gateways dating back to the 19th century. 

Completing the trail around Fort Canning only takes about 45 minutes, but you can take your time exploring each relic and landmark you’ll come across. In total, the trail length is just 2 kilometres, but you can make laps multiple times around the hill.

Some sites you’ll encounter are Fort Canning Centre, the Spice Garden, the Battle Box, remnants of 19th-century fortress walls and cannons, and more. There are about 28 different points of interest in this trail, so you’re spoilt for choice!


You can start the Colonial History Walking Trail via three entrances: Clemenceau Avenue, Hill Street, and Canning Rise. 

If you want to start the trail near the car parks, the closest entrance is at Canning Rise. From there, walk towards the security post and start your trail from the Sally Port or the Battle Box. 

There’s a section inside Fort Canning Park that has staircases, but wheelchair access is available at the Cox Terrace roundabout. 

If you’re travelling with someone who needs walking assistance, stay within the paths from Cox Terrace or ask for assistance from the management at Fort Canning Centre. 

Chinatown Heritage Trail 

– From chinatownsingapore

Starting Point: Chinatown Heritage Centre, 48 Pagoda St

Ending Point: People’s Park Complex, 1 Park Rd

Trail Duration: Around 2 hours 

Trail Length: Around 6 kilometres


A visit to Singapore is not complete without going on a walking tour around its vibrant Chinatown! Singapore’s Chinatown is a bustling neighbourhood packed with temples, preserved shophouses, shopping malls, markets, and hawker centres. 

My recommended trail begins at the temporarily closed Chinese Heritage Centre, ending at People’s Park Complex. Along the way, you’ll encounter 15 diverse sites, including pit stops at Ann Siang Hill and Club Street for refreshments.

Temples to visit along this trail are the Thian Hock Keng Temple, the Buddha Tooth Relic Temple, the Sri Mariamman Temple, and the Masjid Jamae. Telok Ayer Street, Keong Saik Road, and Amoy Street are also included, so get your walking shoes ready! 


The best MRT station to alight when starting the Chinatown Heritage Trail is Chinatown MRT. 

I highly recommend doing this trail in the early morning (around 8:00 am) or late in the afternoon (4:00 pm) to avoid the crowds along Chiantown’s streets. 

Plus, the weather may be chilly during these times, making the walking tour more comfortable for you to complete. 

Both the Buddha Tooth Relic Temple and the Thian Hock Keng Temple are open from 9:00 am to 5:00 pm and 7:30 am to 5:30 pm, respectively. Plan your tour accordingly! 

Colonial District Heritage Trail (AKA Civic District Walking Trail)

Starting Point: St. Andrew’s Cathedral, 11 St Andrew’s Rd

Ending Point: National Gallery Singapore, St Andrew’s Rd

Trail Duration: Around 2 hours 

Trail Length: Around 6 kilometres


Do you have a penchant for museums, colonial architecture, and historical landmarks against the backdrop of a highly urbanised city? If so, the Colonial District Heritage Trail should be right up your alley! 

This trial is another of my personal favourites, mainly because it covers the city’s top five museums and some of the most beautiful colonial structures in Singapore. I can finish this trail in 2 hours, but give yourself extra time to visit ongoing exhibitions. 

On this trail, you’ll visit St. Andrew’s Cathedral, Raffles Hotel, Chijmes, Singapore Art Museum, National Museum of Singapore, Peranakan Museum, Parliament of Singapore, Fullerton Hotel, The Padang, and the National Gallery Singapore!


The sites I mentioned above are just the main landmarks, but you can also spend extra time visiting Armenian Street, the Asian Civilisations Museum, the Victoria Concert Hall, the Central Fire Station, the Armenian Church, and Armenian Street to go full circle. 

Check the website for more details. 

Once you reach the Raffles Hotel, don’t skip out on visiting the Raffles Long Bar. 

This is where the iconic Singapore Sling cocktail was invented in 1915, so getting yourself a round or two of this sweet drink right in its birthplace is a must-do! 

Little India Heritage Trail 

– From yuniqueyuni

Starting Point: Little India MRT Station, 60 Bukit Timah Rd

Ending Point: Tekka Centre, Bukit Timah Rd or Mustafa Centre, 145 Syed Alwi Rd, Mustafa Centre

Trail Duration: Around 2 hours 

Trail Length: Around 6 kilometres


When I think of Little India, vibrant food, colourful temples, friendly locals, bustling markets, and streets adorned with murals immediately spring to mind. This heritage trail encapsulates everything I’ve just described about experiencing Little India!

The trail starts off straight from the Little India MRT Station where you can find vibrant street art adorning the walls along Race Course Road. From there, enter Kerbau Road to find the Tan Teng Niah House, a beautifully preserved Chinese villa built in 1900. 

All the other important sites on this trail are located within walking distance from the Tan Teng Niah House, starting with Tekka Centre. You can binge on Indian food there or make your way towards the Indian Heritage Centre or the Hindu temples nearby! 


There’s no right way to complete this trail since all the important sites are located within walking distance of each other in this small district. If you want to follow a guide, I recommend sticking to the trail guide from this website

I suggest visiting Tekka Centre first before exploring the rest of Little India. The market opens as early as 6:30 am, but many stalls close by 3:00 pm to 4:00 pm. Only a few will remain open in the evening, so plan your tour accordingly! 
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