Labrador & Alexandra heritage tour visits key military installations constructed by the British to defend the naval outpost in Singapore and recounts the series of battles in Labrador and Alexandra prior to the fall of Singapore on 15 February 1942.

With its deep natural harbour and strategic location astride busy shipping lanes, Singapore was the quintessential site for a British port. The offer of free trade and the opportunity to avoid expensive Dutch ports further contributed to Singapore’s success as a trading port. Alongside concepts of free trade, Raffles and his comrades introduced an efficient system of governance that engendered her growth and expansion. On one hand, Farquhar and his compatriots embarked on public works programmes and developed banking and legal systems to facilitate commerce and trade. On the other hand, they abolished customs duties and suppressed smuggling by introducing tough laws. Raffles affirmed that it was more desirable to “make smaller profits on a larger capital than larger profits on a smaller capital.” These policies gave Singapore an absolute monopoly of free-trade in the Malay Archipelago as Singapore became the “Clapham Junction of the Eastern Seas.” By the 1830s, Singapore had supplanted Batavia and Penang as the focal point of the Chinese junk trade and the chief export gateway for gambier, pepper and other spices. Keppel Harbour had also become one of the busiest channel in the world.

Singapore’s success in entrepot trade underline the importance in fortifying the island to defend British’s Far East interests. Fort Pasir Panjang is a former defence battery located within the Labrador Park Nature Reserve, constructed to defend the western entrance to Keppel Harbour. Construction of the fort complex at Labrador was first mooted in 1843 when the British recognised Labrador’s strategic location near the southernmost point in Singapore mainland, which commanded a spectacular view of the entire western anchorage and some of the southern islands. Between 1864 and 1878, concrete bunkers, underground tunnels, gun batteries, two gun emplacements each mounted with a 7-inch muzzle loading gun, a landing site, a gateway with portcullis and a road connecting the two gun emplacements were built and embedded on the coastal cliff-side.

Prior to World War II, Labrador Battery, a secondary battery comprising two 6-inch guns of 1900-1918 manufacture were installed at Fort Pasir Panjang in response to a possible attack by the Japanese battleships. Operated by the 7th Coastal Artillery Regiment, these guns were supported with searchlights and ammunition storage facilities and they were directed southwards, in anticipation of an attack from the sea.

However, these fortifications did not deter or impede the Japanese forces during World War II. On 14 February 1942, the 55th and 56th Infantry Regiment from the 18th Division, led by Lieutenant General Renya Mutaguchi, succeeded in penetrating the Allied defence position at Opium Hill. The Japanese forces gained control of the ridge overlooking the north and attained direct passage to Alexandra Road which held numerous ammunition and supply depots.

An ambush by the 1st Malay Regiment and heavy artillery poundings from the 12-pounder guns at the junction of Pasir Panjang Road and Alexandra Road near Alexandra Brickworks Company killed 94 Japanese troops and halted them from advancing Keppel Harbour through Pasir Panjang Road. As a result, the Japanese 18th Division switched their activities onto the 2nd Battalion Loyal Regiment housed in Gillman Barracks.

A fierce battle raged at Gillman Barracks on 15 February 1942, where close-quarter infantry fighting on wooded slopes and around the barrack buildings took place throughout the day. The 2nd Battalion Loyal Regiment could not hold its position against the onslaught of Japanese artillery attacking from the Tiger Beer brewery and a nearby Alexandra Brickworks Company quarry. By 1600 hours, the 2nd Battalion Loyal Regiment fell back a few hundred yards to fresh positions west of Mount Faber.

The 55th and 56th Infantry Regiment from the Japanese 18th Division pressed further north towards Alexandra Hospital. Within a 30-minute span, the Japanese 18th Japanese Division had brutally assaulted the hospital. Three platoons of soldiers from the 55th Infantry Regiment attacked the hospital simultaneously. It was possible that the initial attack was provoked by soldiers from the 44th Indian Brigade firing from the hospital grounds as they retreated towards the Singapore City.

The first platoon of the Japanese company infiltrated from the railway line around the ancillary buildings towards the hospital front and barracks block. The second made for the rear entrance admission room, medical wards five and six, and the patients' dining room ward. The third came through the windows to the operating theatre block and surgical wards sixteen and seventeen.

The massacre at Alexandra Hospital left more than 200 dead and injured. According to historian Peter Thompson, who interviewed numerous survivors of World War II, the cold-blooded, premeditated massacre was to “show Percival that an utterly mindless and totally ruthless force would be unleashed upon Singapore if he persisted in ignoring Yamashita’s demand to surrender.” At the Singapore General Hospital, Allied troops feared a repeat of the Alexandra Hospital massacre when Japanese snipers opened fire in the hospital grounds. A dejected Percival later signed the instrument of surrender, marking the fall of Singapore to the Japanese.

A decline in entrepot trade after the Great Depression and later, the World War II, prompted the construction of Alexandra Industrial Estate. The establishment of an industrial estate along Alexandra marked Singapore’s drive into industrialisation and diversification from the entrepot economy. Alexandra was chosen for her close proximity to the former Malayan Railways and large labour catchment. Many iconic pioneer businesses including Lea Hin Co (Pte) Ltd, Singapore Telephone Board (Predecessor of Singtel), Malayan Breweries, Alexandra Brickworks Company and Thye Hong Biscuit and Confectionary Factory can trace their roots to the industrial estate.

A myriad of social institutions were pioneered in Queenstown and could be identified along the tour.  For instance, blocks 160 & 161 Mei Ling Street are the first point blocks constructed by the Housing and Development Board in 1970 to reduce homogeneity in public housing. In addition, Queensway Shopping Centre is one of Singapore’s first multi-purpose shopping complexes opened in 1974 to provide shopping and recreational options for residents in Queenstown.