The story behind Dempsey Hill

Dempsey Hill is named after a British commander-in-chief, General Sir Miles Christopher Dempsey (1896–1969), and today is a thriving retail and entertainment hub with a rich heritage. We look back as a salute to the bicentennial …

In the 1850s, Dempsey Hill was known as Mount Harriet, and was part of a huge nutmeg plantation of 1,600 trees, reaching all the way to what is now the Singapore Botanic Gardens. A nutmeg-beetle blight forced the estate to close in 1857 and made the land useless for growing. The owners sold the land to the British Forces in 1860 for a mere 25,000 Spanish dollars.

The Barracks

Singapore had become an important strategic stronghold for the British Empire by this time, and the Tanglin area was the perfect spot for new troops to be kept safe. Ten service barracks for 50 men each were built in the early 1860s, in addition to washhouses, cookhouses, a school and more. The buildings had plenty of windows and doorways to help with air flow – architecture that is now protected by Singapore’s conservation guidelines.

World War II saw the barracks used by the Japanese to store medical supplies and house POWs. After the Japanese surrender, British forces retook Tanglin Barracks, making them the General Headquarters of the Far East Land Forces.

Former British Serviceman Gary Bennet shared his memories from that era: “At the time, there were probably 500 servicemen housed in identical, nondescript buildings in Blocks 7, 8, 9 and 10 at Dempsey Road. They had access to facilities such as a swimming pool and cinema, both now demolished, and a gymnasium overlooking the cricket pitch – a building that still stands today.”

Bennet lived in Block 9 (now REDSEA Gallery), which had enough accommodation for 45 to 50 servicemen. Each block was split into three sections with the middle section used for communal washing, showers and toilets.

New Directions

When the last British forces left in 1976, Singapore’s government took ownership and used “Tanglin Camp” for military purposes. As you walk between Blocks 15, 17 and 18, you can imagine anxious parents gathering to wave off their sons as they reported for conscription back in the 70s and 80s.

The area was vacated in 1989 and gradually the old military barracks were converted into the unique and special enclave it is today.

But even now, you can visit some very special historical spots in Dempsey.

St. George’s Church

This Anglican church was built as a garrison church, only becoming a place for civilians to worship in 1971. During WWII, Japanese forces stored ammunition in the building. Fearing the stained-glass windows would be destroyed, the colonial chaplain had them dismantled and buried. Unfortunately, he died, and nobody knows where those original windows are today. The classical Basilica-style church is now a national monument.

Ebenezer Chapel (The White Rabbit)

The beautifully restored chapel was used as a school for children of British soldiers. This is now a perfect spot to get an exquisite European meal in a stunning setting.

Singapore Civil Service Clubhouse (Samy’s Curry)

Block 25 was originally a sergeant’s mess, but became a clubhouse for Singapore’s civil servants in the 1970s, where inter-territorial games between Singapore and Malaysia were played. Now, the legendary Samy’s Curry occupies the space, still serving the same yummy Indian food it did then.

Old Military Hospital (Loewen by Dempsey Hill)

This special area within the Hill was originally the military hospital that overlooked the housing facilities and the parade grounds. Today, the area has been carefully restored and transformed to an education and lifestyle destination the whole family will love.

Did you know?

The barracks inspired young Rudyard Kipling to write Barrack Room Ballads.

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This article first appeared in the August 2019 edition of Expat Living. You can purchase a copy or subscribe so you never miss an issue!

Melinda Murphy

Melinda does Special Projects for Expat Living which includes pulling together big stories, videos — all sorts of cool stuff. It all builds on her background as a television correspondent, producer and author back in the US. Her life is kind of a special project, too, with two young kids, an old dog, a ridiculous number of volunteer activities — and a very understanding hubby.