Orchard Road Walking Trail

ION Orchard Mall on Orchard Road in Singapore
ION Orchard Mall on Orchard Road in Singapore

By Vicky · Published Feb. 15th, 2022 · Updated Mar. 16th, 2023

See more than glitzy shopping malls on this Orchard Road walking trail that visits the heritage buildings and interesting sights on this busy thoroughfare.

How to get to Orchard Road

There are three MRT stations on Orchard Road, all on the red North-South Line. Dhoby Ghaut MRT station is at the southern, city-centre end of Orchard Road, Somerset MRT is in the middle and Orchard MRT is near the northern end, in ION Orchard Mall. Alternatively, Bencoolen MRT station on the blue Downtown Line and Bras Basah MRT station on the orange circle line are also both near the southern, city-centre end of Orchard Road. This hike starts from the southern end of Orchard Road so Dhoby Ghaut MRT is the best.

Orchard Road Walking Trail Map

Get the route by downloading the .gpx or .kml file below. For navigation with Maps.me on your mobile phone, simply download the .kml file and open to add it to the Maps.me bookmarks.

Tips for Orchard Road Walking Trail

  • Opening hours of the shops and malls is generally 9 am to 9 pm or 10 pm.
  • The food court in the basement of ION Orchard is a popular, affordable place to grab something to eat.
  • Cuppage Terrace or the bars on Emerald Hill Road are atmospheric places to grab a drink or bite to eat.
  • The National Museum of Singapore* and historic Fort Canning Park are close to the start of this trail, while the Botanic Gardens are a 20-minute walk from the end.
  • The evenings are a good time to walk along Orchard Road because most of the sights on this trail are lit up and it’s cooler.
  • Find more walks and hikes in Singapore.

Attractions on the Orchard Road Walking Trail

On this walking trail you’ll see the main sites and attractions of Orchard Road:

  1. Orchard Road Presbyterian Church
  2. Cathay Building
  3. Temasek Shophouse
  4. Istana Heritage Park and Gallery
  5. House of Tan Yeok Nee
  6. Windsor House II
  7. Cuppage Terrace
  1. Sian Teck Tng Convent
  2. Emerald Hill Shophouses
  3. Kuniyika Bookshop & Takashima in Ngee Ann Mall
  4. Ion Orchard Mall
  5. TANGS at Tang Plaza
  6. Goodwood Park Hotel
  7. Thai Embassy
Statues outside ION Orchard Mall in Singapore
Statues outside ION Orchard Mall

History of Orchard Road

As its name suggests, Orchard Road used to look very different to the glitzy shopping mall-lined busy road it is today. Orchards of nutmeg, strands of bamboo, gambier (used in dye) plantations used to grow by the country lane here, giving the road its name. A plant disease in 1857 wiped out the nutmeg orchards freeing up space for retail and development. In the 1980s shopping really took off on this street and it hasn’t looked back since.

Orchard Road Walking Trail Route

This walking trail starts from Dhoby Ghaut MRT station. Try and exit from A.

Directions: From Exit A of Dhoby Ghaut MRT station, head towards the road junction of Handy Road and Orchard Road. You should see the white spire of the first stop.

1. Orchard Road Presbyterian Church

Orchard Road Presbyterian Church

Here since 1878, this old church is very pretty, especially in the early morning or late evening light. It’s also not bad looking when lit up at night. During Colonial times many Scottish people worshipped here since the Presbyterian branch of Christianity began in Scotland.

Many Scottish people left with Independence in 1965 and today the church is full of locals. Services are now in four languages: English, Mandarin, Indonesian and German. You can look around the inside of the church if no service is going on – just ask the staff at the entrance.

Directions: From the church, head left and cross over Orchard Road and then Handy Road to an open space with an art deco mall.

2. Cathay Building

This striking art-deco mall, constructed in 1939, houses a mall and the oldest cinema in Singapore. In the 1950s and 60s, the Cathay Group didn’t just own cinemas but produced films, mainly in Chinese or Malay. Today you can visit the Cathay Gallery (2nd floor, free, open 2-6 pm Mon-Fri and 12-6 pm Sat) inside the mall which explains the history of the Cathay Group’s involvement in film.

Cathay Building on Orchard Road

Directions: Head back over Handy Road and you’ll very soon reach the next stop. For better views, head across Orchard Road back to near the metro station.

Dhoby Ghaut

The name of this area, Dhoby Ghaut, comes from the Hindi word dhoby, which means laundryman. Indian Soldiers in the British Army based at nearby Fort Canning came here in the 1800s to wash their clothes, since a stream that used to run through this area was the closest source of water outside the city centre. Ghaut means riverbank.

3. Temasek Shophouse and Neighbours

This white and black building is a large, gorgeously restored, smart shophouse. Temasek, a holding company owned by the Government of Singapore, owns this building and uses it as the hub of its social impact projects. Foreword Coffee shop is located inside in a lovely, airy space with high ceilings.

Temasek Shophouse on Orchard Road
Historic building in Singapore
SMA Building on Orchard Road in Singapore

The neighbours of Temasek Shophouse are also grand, with stately MacDonald House made of brick on one side, and colourful SMA House on the other. A car showroom previously occupied this distinctive building. The Singapore Manufacturers’ Association (SMA) took it over in 1987, although it’s now used by a learning institute.

Directions: Continue up Orchard Road and soon you’ll see a park-like area with a slightly strange sculpture and water feature in the middle. This is Istana Park.

4. The Istana Heritage Gallery and Park

Festival Arch Sculpture in Istana Park
Festival Arch Sculpture in Istana Park
Gates to the Istana on Orchard Road in Singapore
Gates to the Istana
Istana Park on Orchard Road

Apart from the water feature, which is actually a Festival Arch sculpture and not air-conditioning vents, this little park contains the Istana Heritage Gallery. This gallery can only be visited on guided tours by groups. The gallery is very small and contains mainly artefacts and state gifts that the President of Singapore has received over time.

The Istana / Palace

The Istana (Palace in Malay) is located in a large park opposite Istana Heritage Gallery. The entrance is normally patrolled by a few serious-looking guards, but the gates are often open and you can peek in. The palace and grounds are only open to the public for three days per year, you can check which days here.

The house, or palace, itself is very grand, and brilliant white with Neoclassical features, totally dominating the surroundings. It was built by the British as a replacement for their Government House and now it’s the house of the president (in Singapore the president is mainly ceremonial, while the Prime Minister does all the politics).

Directions: Head to the other side of the park from the Istana Entrance Gates and look across the road for an old yellow building.

5. Tan Yeok Nee Mansion

Tan Yeok Nee Mansion on Orchard Road in Singapore

This is a historic building from the 1880s. The design comes from similar houses in southern China and it was built for a wealthy Teochow trader, Mr Tan Yeok Nee, who made his money from gambier (used in dyes and medicine) plantations. It’s not open to the public, you can only admire the outside.


Many of the older buildings on Orchard Road were originally built by or designed for those in the Teochew (Chaoshan or Chaozhou) Community. This community is from Guangdong Province in southern China and today Teochew is the second most spoken dialect of Chinese in Singapore. Many Chinese left Teochew in the 1800s, hoping for a better life in Singapore and today roughly 20% of Chinese people in Singapore can trace their origins to Teochew Prefecture.

Directions: Continue up Orchard Road, through the park, and further along on the same side is another historic building.

6. Winsland House II

This charming, old white house is behind the strip of trees on the lefthand side of the park. At first it looks like a huge mansion, but it’s actually made up of two semi-detached houses. These were built in the early Edwardian times, around 1915. In the 1990s the buildings were restored to their current condition.

Winsland House II on Orchard Road

Directions: Cross back over Orchard Road and head down a street by The Centrepoint Mall.

7. Cuppage Terrace

Cuppage Terrace
Cuppage Terrace

Cuppage Terrace is a covered row of restored shophouses just next to Centrepoint Mall. It’s more atmospheric at nighttime when the shophouse fronts are nicely lit up and the many bars here fill with people. It’s a decent place to have a drink or bite to eat because you can sit outside without being by the road. However, it does have more of a fake mall feel than the shophouses nearby on Emerald Hill Road, a stop later on this walk.

Cold Storage

Cold Storage is a very old supermarket chain, with its first shop in 1903. It was less of a supermarket back then when they focused on frozen meat and dairy products (that need to be kept in Cold Storage) from Australia.

The Centrepoint Shopping Centre on Orchard Road was actually built by Cold Storage, a first in Singapore. It was also Cold Storage that came up with the idea of importing Friesian cows to Singapore in 1929 to live at Dairy Farm to increase the local supply of milk.

Directions: Continue through the mall and out the other side a little way to glimpse the next spot on the walking tour.

8. Sian Teck Tng Convent

Sian Teck Tng Convent

Sian Teck Tng Convent is not open to the public, but you can admire its outside. The temple building, from 1904, houses a vegetarian convent, also known as Cuppage Temple (after the road it’s on). It is mainly for widows and unmarried women, who perform daily rituals and sacred rites and worship Guan Yin, the Goddess of Mercy.

Directions: Head back to Orchard Road and then up the very next side street, Emerald Hill Road.

9. Emerald Hill Road

Shophouses of Emerald Hill Road
Shophouses of Emerald Hill Road
alleybar at the bottom of Emerald Hill Road
alleybar at the bottom of Emerald Hill Road

This is a lovely, atmospheric little lane surprisingly just off Orchard Road. Charmingly atmospheric bars occupy the shophouses nearest Orchard, but if you pass these you’ll reach a peaceful residential area of charming shophouses. Stroll up the hill and admire the architecture and classic five-foot ways linking the buildings.

Directions: Return back to Orchard Road and head right towards the business end of the road, jam-packed with luxury designer shops.

10. Ngee Ann City

Ngee Ann City
Kinokuniya Bookshop in Takashimaya Department Store in Ngee Ann City Mall

Ngee Ann City Mall was built on a former Teochow Graveyard by Ngee Ann Kongsi (a charitable Teochew foundation/clan association). Today it’s home to Takashimaya, a posh Japanese department store containing luxury goods from Japan and many expensive restaurants. One of the best shops is Kinokuniya, a large bookshop selling books and magazines in English, Japanese and Mandarin.

Directions: Continue further along the road and you’ll soon see a strikingly-modern mall on the left.

11. ION Orchard Mall

ION Orchard Mall in Singapore

This flashy, modern mall is full of designer shops. While the luxury shops are often fairly empty, the basement contains a food court which is always busy. Many people come here just to take a photo with the colourful people statues on the steps by the entrance.

Directions: Cross over Orchard Road to the mall on the other side. To cross the road here you’ll need to take an escalator down to a shop-lined underground walkway leading across the street. It’s very easy to get confused once underground and hard not to end up in ION Orchard Mall. Follow the signs for TANGS. You should come up just outside this mall.

12. TANGS at Tang Plaza

Distinguished by its pagoda rooftop, Tang Plaza dates back to the 1950s and was one of the first malls to open on Orchard Road. Mr Tang, a lace salesman from China, thought the location of Orchard Road ideal, as it was close to residential districts and on the route between downtown Singapore and Johor in Malaysia. He wanted a green-tiled roof with red columns and pagodas to create a distinctive and memorable place to attract customers. TANGS is known today for including more Singapore-based designers than the other malls.

 TANGS at Tang Plaza on Orchard Road

Directions: Head up Scotts Road, a main street crossing Orchard Road, and in 400 metres you’ll see the next stop.

13. Goodwood Park Hotel

Goodwood Park Hotel in Singapore

The Germans built Goodwood Park Hotel in 1900 as a social club called Teutonia Club. The British took it over during the First World War and today it’s a heritage hotel and architectural gem. You can admire the outside, designed to look like a German Castle, and pop into the lobby to check out the inside and perhaps take some tea.

Directions: Return to Orchard Road and head right to visit the final stop on the walking trail. You can either cross on the pedestrian bridge or try to navigate the underground crossing again, this time going across Scotts Road. If you attempt this, do read the signs or you’ll undoubtedly end up back in ION Orchard.

14. Royal Thai Embassy

The Royal Thai Embassy is a historic building on Orchard Road. Today it looks rather out of place among the gleaming shopping malls. The Thai King Rama V bought a mansion here in the 1890s when presumably prices were a little lower than today. He later sold it but the Thai government decided they liked the location so they bought the place in 1897. The Royal Thai Embassy that you see here now was built rather later, from 2010-2017.

Royal Thai Embassy in Singapore

Directions: This is the end of the walking trail. There’s a bus stop just outside the Royal Thai Embassy. Alternatively, you can return to ION Orchard Mall for Orchard MRT Station on the red North-South line.

Other Sites within Walking Distance to Orchard Road

If you want to walk further, you can continue along Nassim Road to the Singapore Botanic Gardens, 20 minutes walk away. Or you can head to Tudor Court just around the corner, a row of cute terraced houses in mock Tudor-Elizabethan style that now contains many shops.

If you head further towards the city from the start of the trail, you’ll soon reach the National Museum of Singapore. Behind that is Fort Canning Park – a lovely park and landscaped hill full of history.

Orchard Road at Night

Cathay Building Mall on Orchard Road at nighttime
Gucci Advert in Singapore
Presbyterian Church on Orchard Road at nighttime
Tang Plaza on Orchard Road at nighttime

Orchard Road is a great place to explore at nighttime since lights shine out from the buildings. The shops and malls are almost all open till 10 pm and it’s much cooler in the evenings.

If you want to experience more culture in Singapore, check out our Kampong Glam Walking Trail, Little India Walking Trail, Tiong Bahru Walking Trail or Chinatown Walking Trail. For more walks and hikes in Singapore, visit our Singapore Guide.

Shophouses on Emerald Hill Road
Shophouses on Emerald Hill Road

FAQS – Orchard Road Walking Trail

What is Orchard Road known for?

Orchard Road is known mainly for its high-end, luxury shopping experience. However, there are also some historical and architectural gems that you can visit on this walking trail.

How to get to Orchard Road?

There are three MRT stations on Orchard Road, all on the red North-South Line. Dhoby Ghaut MRT station is at the southern, city-centre end of Orchard Road, Somerset MRT is in the middle and Orchard MRT is near the northern end, in ION Orchard Mall. Alternatively, Bencoolen MRT station on the blue Downtown Line and Bras Basah MRT station on the orange circle line are also both near the southern, city-centre end of Orchard Road.

Leave a comment

Your email address will not be published. Required fields are marked *