City Hall running trail

Duration: 1 hour

Distance: 3.25 kilometres

Difficulty level: Medium. There is uphill terrain and a winding route.

A bustling neighbourhood by day, City Hall unwinds when the sun sets and office warriors head home. Take advantage of the almost-bare streets and loosen up your tie as you embark on an after-work run. Among the cluster of tall buildings, the city centre is also a history-rich area, which has witnessed plenty of Singapore’s milestones in her road to independence.

Unleash your inner history geek while releasing endorphins on this hour-long, 3.25-kilometre heritage running trail, which takes you around the district to uncover architectural gems and prominent heritage sites from the colonial era.

All venues are near the City Hall MRT station
Fort Canning Park

Start at 1 Fort Canning Park and breeze past the white Gothic gates at the entrance to begin the trail. The hilltop garden, formerly known as “Forbidden Hill”, was once home to the ancient Malay rulers of the island before the British officials transformed it into a fort in 1860. Warm your muscles up by tackling the sloping terrain to reach the former British army barracks at the top. Get charged up as you come face-to-face with one of the remaining nine-pound cannons that were used in the past. Run along the designated pathway—there are fragments of the fort wall, and a variety of indigenous flora, such as the elephant ear fig tree and ear-pod tree. A visit to the Battle Box, an old underground bunker, which functioned as a command centre during the war, will serve as a stark, yet important, reminder of the country’s history during World War II.

There are plenty of museums located in close proximity, too, including the National Museum of Singapore, Singapore Philatelic Museum and the Central Fire Station. Head down Canning Rise towards Coleman Street, and make a quick pit stop at the national stamp museum. The building also operates as a sub-post office, where you can drop off your mail at the only operational colonial postal box left in the country. For a more memorable moment, pose with the bright, red cylinder-shaped postbox and take a selfie.

Civilian War Memorial

After taking your souvenir snapshot, make a dash towards the War Memorial Park on Beach Road. Located at the centre of the park is the 2 The Civilian War Memorial, otherwise recognised as ‘The Chopsticks’ by locals. The monument honours the thousands of civilians who died during the Japanese Occupation of Singapore, and the four pillars were designed to signify the nation’s main ethnic groups: Malay, Chinese, Indian and Eurasian.

National Gallery Singapore
Photo by Darren Soh

Next, travel west in the direction of St Andrew’s Road towards National Gallery of Singapore. Pace yourself so you don’t miss the St Andrew’s Cathedral on your right. It is the country’s largest church and oldest place of worship for Anglicans. The institution shows off the intricate designs inspired by early English Gothic architecture, featuring high steeples, wide stained glass windows and a grand nave.

Just a short distance away is the 3 National Gallery: 8,000 Art Pieces of Southeast Asia. The two buildings that comprise the gallery were formerly occupied by the Supreme Court and City Hall before they were converted into the majestic art landmark you see today. The venue still retains its historic exterior, especially its famous blue dome. Monumental events, such as the surrender of the Japanese forces and Singapore’s Merdeka speeches, also took place on the very steps of the building’s main entrance.

Take a breather and stop for more photo ops—head up to the Ng Teng Fong Roof Garden Gallery to get a view of the city’s Central Business District (CBD) skyline.

Asian Civilisations Museum
Photo by Afur Wong

Continue your run towards Empress Place, where you will notice more examples of colonial-era structures in the area. Overlooking the Singapore River is the 4 Asian Civilisations Museum, which was once known as the Government Offices. The museum now houses a collection of ancient artefacts that chart the heritage of Asia and Singapore’s history as a port city.

A few strides away from the museum stand The Arts House and Victoria Theatre and Concert Hall. Standing tall and gleaming with pride among them is a bronze statue of Sir Stamford Raffles, the founding father of modern Singapore. Break your momentum and stop for a selfie with the iconic landmark while you’re there.

Esplanade – Theatres on the Bay

Cut your way through Esplanade Park, and be greeted with more tributes to the fallen victims of World War II. Here stands the Lim Bo Seng Memorial, a pagoda-looking construction with influences from Chinese National style of architecture. It is also the only national monument that commemorates a notable Singapore war hero. Further down the park, you will see The Cenotaph, which features the engraved names of the soldiers who fought during the war-torn period.

Complete your last lap at 5 Esplanade - Theatres on the Bay. Apart from being a popular arts hub, the venue is also often identified by its intriguing roof design—many locals draw similarities to the durian. To cool down, venture to its rooftop terrace where you’ll be able to do your stretches and take your post-run selfie against a stunning panoramic view of the Marina Bay Sands®.

End your run by chilling out at the bars and restaurants in the area. For a taste of local street food, pop by Makansutra Gluttons Bay and replenish your energy with a generous plate of fried carrot cake accompanied by a tall, cold glass of sugarcane juice. After eating your fill, hang in the area and you might be able to catch a couple of free gigs that’s occasionally hosted at the outdoor theatre.