18 Experiential Walking Trails in Singapore you will enjoy

Getting around in Singapore is easy. There are bus stops at every corner, at least one MRT station at every district, and taxis readily available just by sticking your hand out by the road or booking on an app. But if you really want to explore Singapore, the best way to do so is to walk. It’s easy to think of Singapore as nothing but a bustling city-state, but there are plenty of forgotten spots, historical monuments, and beautiful natural landscapes to discover at every turn. Want to see them for yourself? Here are 18 Singapore walking trails you have to check out, no matter if you’re a tourist or a local.

1. Of Graves, Guns & Battles

Gain a deeper understanding of the life of soldiers in Singapore during World War II with this informative walk, aptly titled Of Graves, Guns & Battles. You’ll be taken to Fort Canning Hill and the Battle Box, a former WWII command centre, along with old graves and a colonial fort.

Organised by: The Original Singapore Walks
Price: $32 for adults; $15 for chldren
Dates: Every Monday and Thursday, 2pm – 4.30pm
More info here: https://www.journeys.com.sg/tosw/our-tours/

2. Journey to Hell

Journey to Hell

Need to do something different for a Friday night out? How about taking a walk to hell and back?

You are challenged to experience Haw Par Villa after dark – if you dare! In this 2 hour tour, you will go through the famous 10 Courts of Hell and learn about the stories of the netherworld. Legends and folklore aside, you will discover the rich philosophies and culture reflected in the park’s eclectic sculptures and dioramas. This is a tour experience finalist, so stated on the website, and definitely worthy of your time.

Price: $18 for adults; $9 for children
Dates: Every Friday, 630pm – 830pm
More info here: https://www.journeys.com.sg/tosw/our-tours/

3. Singapore-After-Dark Night Tour

On this 4-hour guided tour, you’ll be covering the best of Singapore nightlife. First experience an authentic hawker night dining experience in town, then explore the vibrant hangouts along the Singapore River, including visits to an exclusive rooftop bar and popular local pub.

The tour ends at Clarke Quay, Singapore most popular nightspot, where you have multiple options to party all night long! Enjoy 2 x complimentary cocktail/beer & snacks.

Organised by: Monster Day Tours
Price: From S$95/pax
Dates: Tuesdays / Thursdays / Fridays
Duration – 4.0 hours
More info here: Monster Day Tour

4. Joo Chiat/Katong Food Walk

There’s no better way to get to know a city than through its food. Enjoy more than 30 traditional and celebratory dishes across Malay, Peranakan, and Eurasian cultures during this evening trail. Tuck into savoury delights and delve into the history of the rich cultural diversities that make the area so special.

Organised by: Betel Box Asia
Price: $80 per person
Dates: Every Thursday, 6:30pm – 12:30am
More info here: http://www.betelboxtours.com/tour-detail/543c0d43da81622766496464/joo-chiat-katong-food-walk

5. “Balik Kampong” Walk

Roam where royalties once resided in Singapore — yes, royalty! Visit the palace grounds of kings and princes of old to have a taste of life in pre-modernised Singapore. Be in store for surprises as this eclectic trail lets you traverse the oldest shopping streets in Singapore through laneways filled with gorgeous graffiti.

Organised by: Indie Singapore
Price: Free
Dates: Every Wednesday
More info here: http://www.indiesingapore.com/our-tours.html

6. Wet Market Adventure

There is not much to say about the legendary Tekka Market, aside from the fact that it’s the marketplace for the best cooks to get their ingredients. While it was initially a slaughterhouse, it has been transformed into one of the busiest and expansive wet markets in Singapore over the years. Instead of just grocery shopping, grab delicious local grub within and around the market too!

Organised by: Wok ’n’ Stroll
Price: $80 per person
Dates: Availability on booking
More info here: http://www.woknstroll.com.sg/culinary-stroll

7. MacRitchie Walk

Lots of Singapore walking trails are about heritage. Not many are about nature! Trek through this forest trail with an experienced guide and learn more about the history of the MacRitchie forest, one of Singapore’s rare natural attractions. Bask in the charming landscape of the forest floor and soak in the breathtaking panorama on the TreeTop Walk. Its beauty will leave you craving more.

Organised by: Love MacRitchie
Price: Free
Dates: Selected Saturdays and Sundays
More info here: https://lovemacritchie.wordpress.com/love-macritchie-walks/

8. Walking in the Footsteps of our Foremothers

Ever wondered who the female heroes of Singapore’s history are and the stories behind their travails? Reminisce their accomplishments during this trail as you visit nine iconic landmarks, such as the Sculpture Square and St. Andrews Medical Dispensary. Be inspired by these superwomen for their past actions and contributions to Singapore.

Organised by: Singapore Council of Women’s Organisations
Price: Free
Dates: Own time, own target
More info here: https://roots.sg/Roots/visit/trails/walking-in-the-footsteps-of-our-foremothers

9. World War 2 Trail

While it has been over 70 years since World War II, there are still scars that have not healed on our shores. The trail consists of 13 spots that mark great historical events that occured during World War II. Visit past battle sites on this trail to understand more about the WWII invasion and explore the locations where the Sook Ching massacres took place. Remember to give a moment of silence to our fallen comrades while you are on this trail.













via roots.sg

Organised by: National Heritage Board
Price: Free
Dates: Own Time, own Target
More info here: https://roots.sg/Roots/visit/trails/world-war-2-trail

10. Pulau Ubin Walk

Not all Singapore walking trails are on Singapore island. Take a brief respite from the busyness of the mainland and make the trip to offshore Pulau Ubin. It’s more than just an idyllic coast to relax in — explore old kampongs (a.k.a. villages), visit historical sites like the Old Bin Kiang School and Tua Pek Kong Temple, and get in touch with the bounty of nature all around the island.

A post shared by AntonioLeón (@antoonio07) on Apr 4, 2018 at 3:02pm PDT

Organised by: NParks
Price: $60 per group, with a maximum of 15 people in a group
Dates: Availability on booking
More info here: https://www.nparks.gov.sg/activities/workshops-and-guided-walks/c-pulau-ubin

11. Kent Ridge Park Walk

It’s hard to believe that this lush public park was the backdrop to one of the fiercest battles between the Malay Regiment and Japanese forces during World War II. Let yourself be taken back in time to experience history firsthand. At the same time, you get to learn more about the intriguing flora and fauna that now cover the landscape.

Kent Ridge Park

Organised by: NParks
Price: $7.50 per person
Dates: Availability on booking
More info here: https://www.nparks.gov.sg/activities/workshops-and-guided-walks/a-hortpark-and-southern-ridges

12. Tanglin Halt & Margaret Drive Walk

Trace the development of Singapore’s first satellite town, Queenstown, with this guided tour that will take you to landmarks along Tanglin Halt and Margaret Drive. Check out lesser-known historical sites like the very first HDB flat (Singapore’s most prominent type of housing), the now-defunct Malayan railways and unique black and white bungalows at Wessex estate. You’ll also get to speak to residents who will share their memories of living in the area.


A post shared by Kathy Boyd (@kathymcd4) on Mar 19, 2018 at 9:47pm PDT


Organised by: My Community
Price: Free
Dates: Every last Sunday, 8.45am
More info here: http://mycommunity.org.sg/tanglin-halt-margaret-drive.html

13. Alexandra & Dawson Walk

If you know anything about history, you’d definitely know a thing or two about World War II. Now experience one of the largest global wars from the perspective of the Japanese troops, through military installations like the former British Military Hospital and military bunkers. Immerse yourself in the past with tales from villagers who went through the war themselves.

Organised by: My Community
Price: Free
Dates: Every last Saturday, 8.45am
More info here: http://mycommunity.org.sg/alexandra-dawson.html

14. My Community @ Katong Trail

One of Roots’ Singapore walking trails, this is specially curated by the students of CHIJ Katong Convent. This trail highlights the most interesting and distinct food, architecture and culture of the eclectic Katong district. Eat your way through the iconic street, and savour traditional Singaporean coffee, laksa, and more while discovering rare conserved terrace houses and age-old religious monuments.

Organised by: CHIJ Katong Convent
Price: Free
Dates: Own time, own target
More info here: https://roots.sg/Roots/visit/trails/my-communitykatong-trail

15. Knowledge is Power

Singapore’s education system may be world-renowned now, but it all started with the sincere efforts of individuals who pooled everything they had to educate the young. Find out who they are and the lengths they had to go through in this informative walk into some of Singapore’s oldest educational institutions.

View this post on Instagram


A post shared by @ jinstg on

Organised by: National Heritage Board
Price: Free
Dates: Own time, own target
More info here: https://roots.sg/Roots/visit/trails/knowledge-is-power

16. Toa Payoh Trail

Many of Singapore’s firsts happened in Toa Payoh town. It’s the first to be entirely developed by the Housing and Development Board (HDB), was the site of the first MRT station, and much more. Steep yourself into the unique significance of this seemingly quiet area by taking this trail to nine of its most iconic landmarks. Be sure to have a go at the Dragon playground, one of the few concrete-and-sand playgrounds left in Singapore!

Organised by: National Heritage Board
Price: Free
Dates: Own time, own target
More info here: https://roots.sg/Roots/visit/trails/toa-payoh-trail

17. Eclectic Escapade

Taste, see, smell, hear and feel the energy in the air as you immerse yourself in the bustling streets of Little India. Check out new kids on the block, along with household names like Muthu’s Curry and the famous Mustafa Centre. Be sure to leave an entire day for your trip here — just getting through Mustafa Centre alone will take you hours.

View this post on Instagram


A post shared by Cedrick (@cdrckcpt) on

Organised by: Singapore Tourism Board
Price: Free
Dates: Own time, own target
More info here: https://roots.sg/Roots/visit/trails/eclectic-escapade

18. Sungei Buloh Walk

Nature-lovers, you have to sign up for this guided tour through Sungei Buloh, another one of the few Singapore walking trails that will take you deep into the heart of nature. The wetland reserve is home to hundreds of wildlife, including mudskippers and mud lobsters, and numerous indigenous plants. As the mangrove is a stop-over point for migratory birds, you might even be able to get a glimpse of never-before seen feathered friends.

Organised by: Sungei Buloh Wetland Reserve
Price: Free
Dates: Every Saturday, 9.30am – 11am
More info here.


Bonus: LocoMole Singapore Walking Trails

If you’re the type of person who prefers to explore at their own pace, then why not try one of LocoMole’s Singapore walking trails? Take your pick from heritage trails for the history buff to relaxing food-and-shopping trails. Don’t say we bojio.

Organised by: You!
Price: Free
Dates: Whenever you’re free.
Download here:



Leave a Comment