Dempsey Hill : Well-loved lifestyle destination

Dempsey hill is filled with gourmet grocers , art galleries, cafes , upmarket restaurants and bars.  The appeal of Dempsey Hill lies in its colonial charm while giving off an idyllic and tranquil ambience. Regardless of day or night, there is something for everyone to look forward to in this charming lifestyle destination.

Naming of Dempsey Hill

Dempsey Hill was named after General Sir Miles Christopher Dempsey, a well respected and established officer in the British Army. Dempsey was born in 1896 and passed away at the age of 73 in 1969. The early parts of Dempsey military career Brought him to serve in North Africa, Sicily and Italy. During those periods, Dempsey built up his reputation for his expertise in combined operations. Thereafter, he was assigned as the commanding officer of the Second Army which formed the main British forces participating in the D-Day landings in 1944. The Second Army completed successful assaults at Gold, Juno and Sword beaches together with Canadian forces.

In 1945, Dempsey was appointed as the Commander-in-Chief of the Allied Land Forces South East Asia (ALFSEA) and the General Officer Commanding of the Malaya Command , with both unit headquartered in Singapore. Despite his long dedication of service to the British Army that spanned two world wars, Dempsey is relatively unknown as he kept himself out of the limelight and is a humble man. Today, Dempsey Hill serves to honour his memory and contributions.

Fun Fact : Several roads around Dempsey Hill were also named after British Commanding Officers - Harding , Loewen , Ridout and Malcolm Roads.

Dempsey Hill History

In the 1850s, the area was part of a large nutmeg plantation known as Mount Harriet. The plantation has over 1,600 trees and was owned by British colonial treasurer William W. Willans and local businessman Whampoa Hoo Ah Kay. In 1857, a blight caused by the nutmeg beetle decimated the plantation, resulting in the closure of the plantation. 

In 1858, Colonel George Collyer , Chief Engineer of the Straits Settlements, arrived in Singapore and was tasked to settle the accommodation of British reinforcement troops who were due to arrive. He scouted various areas and found the Tanglin area to be suitable for housing the troops , hence, the British forces purchased the plantation for 25,000 Spanish dollars in May 1860.

Construction began on the 213-acre site to convert it into Tanglin Barracks to house British military troops. There were ten buildings in total and each building could house 50 soldiers. Other facilities included cookhouses , hospital wards , school, library, reading room and officers’ quarters.

The original structures at Tanglin Barracks were designed to increase airflow by incorporating lots of windows and doorways. Wooden floors, plank walls and thatched roofs are also features that help the incoming European regiment combat the tropical heat . In 1911, the thatched roofs were replaced with more durable red French tiles.

The construction of the Tanglin Barracks was completed in 1861. However, it was left empty until 1867. In preparation for the arrival and accommodation of the 80th Regiment Foot Staffordshire Volunteers, the Barracks underwent further renovations to add a 240 bed Tanglin Hospital. 

Major C H Malan, Commanding Officer at Tanglin Barracks from 1868 to 1870, noticed the poor living conditions of the area and sought improvements to raise the welfare of his soldiers. Milan ordered soldiers to clear the dense vegetation and replace the cleared area with facilities such as a cricket field, rifle range, gardens and gymnasium. Milan also requested for a garrison church to be built inside the perimeter of Tanglin Barracks.

While World War I was ongoing, on 15 February 1915, a group of Indian soldiers from the 5th Light infantry carried out a mutiny against the British forces in Singapore. The British forces were caught unprepared as most of the troops were deployed to fight the war in Europe and 15 February 1915 was also the Chinese New Year, a major festival in Singapore. The Indian soldiers shot at any Europeans they came across in their tracks. The Indian soldiers broke into the prisoner-of-war camps near Tanglin Barracks, freeing 300 German prisoners and providing them with weapons. They also advanced to Tanglin Barracks and killed 13 soldiers. 

There was widespread fear and chaos as Martial Law was swiftly implemented in Singapore. European women and children were quickly moved to ships in the harbour, ready to evacuate should the necessity arise. Eventually, it lasted a week as reinforcements from other British and Allied forces helped to suppress the mutiny.The incident came to be known locally as the “1915 Indian Mutiny”.

During World War II, Singapore fell to the Japanese with the official surrender of the British forces on 15 February 1942. The British and Australian soldiers defending Singapore became prisoners of war , gathering at Tanglin Barracks before their long march to internment in Changi.

When World War II ended, British forces regained control of Tanglin Barracks and designated it as the General Headquarters of the Far East Land Forces. This continued until the British withdrawal from Singapore in 1971. On 10 February 1972, Tanglin Barracks became the headquarters of Ministry of Defence (MINDEF) and Central Manpower Base (CMPB), where 18 years old young men enlisted for their National Service. Tanglin Barracks was also used by MINDEF as the area to consolidate the majority of its key command and support branches in a centralised location. 

MINDEF and CMPB occupied Tanglin Barracks until 1989, when MINDEF relocated to Bukit Gombak while CMPB relocated to Depot Road. Tanglin Barracks was vacated and handed back to the Land Office and it was subsequently leased out to the private sector.

In 2006, the Singapore Land Authority (SLA) rebranded the area as Tanglin Village, a 40-hectare site. Tanglin Village was also used as one of the exhibition sites for the Singapore Biennale in November 2006. Shortly after, SLA called for a tender to transform Tanglin Village into a site for lifestyle, education and the arts. A property investment company called Country City Investment won the tender and invested about S$3million to develop the area. The area was officially launched as Dempsey Hill on 12 July 2007, comprising of retail, recreational and restaurants outlets.

Directions : 
Travel to Napier MRT (TE12) and go to the bus stop outside (Napier Stn Exit 2). Take any bus that comes along (Bus 7,75,77,105,106,123,174) and exit 2 bustops later at CSC Dempsey Clubhouse. Take the stairs up to Dempsey Hill

If you are making a trip to Dempsey Hill, take the chance to check out the Musuem of Ice Cream which is located nearby.

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