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Hero Video Credit: 13 Tips for an AWESOME Trip to Singapore Matt's Travel Tips

Hero Image: Amazing colorful decorative painted wall at Haji Lane. Street art by an unknown artist at the Muslim quarter (Arab quarter) in the Kampong Glam. Graffiti in Singapore.

Singapore may be best known for its cosmopolitan architecture, and buzzing city life; however, if you’ve been bit by the wanderlust bug, and are looking to explore the rich heritage of the Lion City, 'on foot' - we’ve got you covered!

Get immersed in the history, and the stories behind iconic Singapore landmarks with these heritage tours that you won’t need a guide for! If you prefer to be guided and in a group reach out to Jane's Singapore Tours - They are the best in town and recognised as a leader. For those readers who like to go commando - this article is for you.

From the influence of Indian immigrants, to the public works of art on display, and the aftermath of World War II, our Expat Choice Ambassadors have created a comprehensive list of the historical trails that will guide you through the legacy of this awesome city.


Orchard Heritage Trail

Video Credit : Orchard Road Singapore to Singapore Botanic Gardens Travel Guide Discovery Walking Tours TV

What if we told you that Orchard Road was so much more than a shopping destination, and tourist hotspot? Previously home to nutmeg orchards (hence the name), Orchard Road is home to a vast history spanning centuries! Get acquainted with the historical landmarks during the Historical Gems tour, learn about the culture and the people behind this iconic location with the Communities and Cemeteries tour, or explore the greenery and beauty of the Butterfly Trail and Singapore’s first UNESCO World Heritage Site on the From Orchard to Garden trail.


Little India Heritage Trail

Video Credit: Little India Singapore By Night Walking Tour Discovery Walking Tours TV

Traipse down the trail that provides a peek into the life and culture of Indian immigrants on the marvelously named Dhobis, Saris, and a Spot of Curry walking tour. Check out Little India’s oldest restaurant, and get your shopping on at the famous Tekka Market. The roughly three-hour tour happens every single Tuesday at 9:30 am so you can plan your schedule accordingly. We’d advise you to dress a tad modestly if you’re planning to enter any mosques and temples on the tour!


World War II Trail

While we often acknowledge the effect that World War II had on Europe and America, Asian countries too bore the burden of the war, and this trail shows the affect of the Japanese Occupation of Singapore. Start at Sarimbum Beach where the invading troops landed, and take a journey through history, from the battle at Bukit Timah, to the Keppel Harbour, and see how this resilient island forged past its most trying times.


Amara Heritage Trail Sentosa

Make the most of the weekend as you discover the interesting history behind Amara Sanctuary Resort Sentosa. Once a former British military site, you’ll be able to take an hour trek through the massive 10 acre property, and even check out the last two air raid shelters from World War II. Priced at $18 a head, you get a $6 discount if you stay at the hotel and make a short staycation out of the trip!


Toa Payoh Trail

Video Credit : Toa Payoh - Balestier Heritage Trail. Airborne 110670

One of the first major towns planned by the Housing and Development Board, Toa Payoh is a veritable goldmine of historical landmarks and an integral part of Singapore’s great national experiment. The trail covers a distance of a little over a kilometer and 12 different places including the Church of the Risen Christ, the 1973 SEAP Games Village, and the Lian Shan Shuang Lin Monastery.


Ang Mo Kio Heritage Trail

Developed in the 1970’s, Ang Mo Kio is a perfect example of the quintessential neighborhood planned by the Housing and Development Board in Singapore and is chock-a-block full of memories and history. A locale so vast that it has two separate trails dedicated to the area, you can check out the town council, St. Thomas Orthodox Syrian Cathedral, the former Sembawang Hills Circus and more on the Ang Mo Kio trail!


Tiong Bahru Heritage Trail

Video Credit : River Valley Singapore to Tiong Bahru Market Singapore Travel Guide Discovery Walking Tours TV

A small, charming housing area, Tiong Bahru has its fair share of famous eateries and local shops, but there’s so much more than that! Explore Bird Corner and the former Hu Lu Temple, and the Monkey God Temple. Surrounded by chic cafes and eateries, where you can drop in for a quick bite, Tiong Bahru truly emulates the phrase ‘where past meets the present’.


Bedok Heritage Trail

A trail exploring Bedok’s history as a former coastal town – did you know that the sea used to come all the way to Marine Parade Road? Bedok trail traces the path from before the development of the East Coast area, and showcases Chai Chee, Fengshan, and Simpang. You can even visit Frankel Estate where Albert Einstein once visited in the 1920’s, and eat at Hua Yu Wee restaurant, the last of the popular seafood restaurants from before the land reclaimation.


Sepoy Lines Trail

The Sepoy Lines Trail will give you a glimpse through the lives of the Sikh community who immigrated to Singapore. Known for contributing greatly to the military outfits of their countries, the trail will go past the former Outram Prison, and Sikh Barracks, as well as the Bhai Maharaj Singh Ji Memorial.


Geylang Serai Foot Trail

Video Credit: Geylang Singapore By Night Walking Tour Discovery Walking Tours TV

Walking on the Geylang Serai Foot Trail, you’ll be astounded by the extent of how much Singapore is a multi-racial, multi-religious, and multi-cultural community! You’ll get a chance to visit the Amitabha Buddhist Centre, Coronation Baptist Church, Eastern Aerated Water Company, pre-war shophouses and Khadijah Mosque on your walk.


Queenstown Heritage Trail

Video Credit : Queenstown Singapore Walking Tour Discovery Walking Tours TV

You can choose from three different guided tours when exploring the Queenstown Heritage Trail which cover their colourful social history, and the evolution of Singapore’s first satellite town. Chat along the way with older residents to get first hand information, and check out Princess House and the former Thye Hong Biscuit and Confectionary Factory for an interesting experience – it’s more than just IKEA!


Jalan Besar Heritage Trail

Video Credit : Jalan Besar Singapore to Lavender Singapore Walking Tour Discovery Walking Tours TV

You’d never believe that Jalan Besar was formerly swamplands, because now it’s a bustling urban neighbourhood, home to shophouses, temples, schools, and housing developments. Take a gander through the former New World and imagine what life could have been like without any modern forms of entertainment. Visit some of their better known historical buildings like the Allenby House, the Hong San See Chinese Temple, and the famous Sri Manmatha Karuneshvarar Temple.


Public Art Walking Trail

If you’re an art enthusiast, and want the opportunity to take a look at some of the most amazing public works of art created by Singaporean artists, then this trail is for you! You’ll get to see many different mediums and styles of art that have become iconic in the present day. Keep an eye out for bronze sculptures by some of Singapore’s pioneers like Aw Tee Hong, Chong Fah Cheong and Lim Leong Seng, and statuesque stone works by female artists, Han Sai Por and Liu Jilin.


Jurong Heritage Trail

This trail will demonstrate why Jurong is so much more than just an ‘industrial town’, because it’s home to interesting markers that you can visit on your own; like an old drive in cinema, the city’s first ever hawker centre Yung Sheng Market, and the Garden of Fame where you can scout out trees planted by visiting premiers like Queen Elizabeth II! Don’t forget to take time out to visit Jurong Lake during your expedition.  


7 January 2020
Singapore may be best known for its cosmopolitan architecture, and buzzing city life; however, if you’ve been bit by the wanderlust bug, and are looking to explore the rich heritage of the Lion City, 'on foot' - these guys have got you covered!


Hot Find
7 January 2020
Toa Payoh Town is the first town designed and developed entirely by the Housing & Development Board (HDB). As the HDB's first major town project, Toa Payoh became a model for public housing in the 1960s. This town is also known for many of Singapore's first, such as the first cooperative supermarket and first Mass Rapid Transit (MRT) station. This trail covers some of the landmarks including religious institutions, burial grounds and health centres. The history of these places are intrinsically tied to the social memories of the residents who lived there and those who continue to call Toa Payoh their home. https://www.roots.sg/Roots/visit/trails/toa-payoh-trail


7 January 2020
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. This trail is by the Geylang Serai Integration & Nationalisation Champions (INC) Committee. https://www.roots.sg/Roots/visit/trails/geylang-serai-foot-trail