Dis­cov­er­ing a dif­fer­ent side of Dempsey.

Expat Living (Singapore) - - Life & Family -

You prob­a­bly al­ready know some of the eclec­tic bou­tiques, eater­ies and bars dot­ted around tran­quil Dempsey Hill. You might even know that its sprawl­ing blackand- whites were once mil­i­tary bar­racks. But did you know about the 1915 In­dian Mutiny, or the mys­tery of St. Ge­orge’s stained glass win­dows?

The hill’s his­tory dates back to the 1850s when it was known as Mount Har­riet, and the Dempsey Her­itage Trail walks you through it all. Part of a huge nut­meg plan­ta­tion co-owned by lo­cal busi­ness­men Wham­poa Hoo Ah Kay and Colonel Trea­surer Wil­liam W. Wil­lans, it was sold off to the Bri­tish forces in 1860.

The Brits then set to build­ing up the Tan­glin Bar­racks that pro­vide the set­ting for to­day’s life­style and shop­ping hub. The name Dempsey came much later still, in hon­our of Gen­eral Sir Miles Christo­pher Dempsey, the 1945 Com­man­der-in-chief of the Al­lied Land Forces South­east Asia which was head­quar­tered in Sin­ga­pore.

While the orig­i­nal palm- thatched roofs were re­placed with red French tiles in 1911, lit­tle else has changed about Dempsey’s clas­sic, colo­nial-style ar­chi­tec­ture. Built to com­bat the trop­i­cal heat, the build­ings fea­ture square col­umns and wrap-around ve­ran­dahs as well as raised floors and lots of win­dows and door­ways. This kept the bar­racks as breezy as pos­si­ble for the in­com­ing Euro­pean sol­diers and keeps to­day’s pa­trons com­fort­able as they ex­plore all Dempsey Hill has to of­fer.

Walk­ing the Her­itage Trail takes you back through the ages to dis­cover the sto­ries of ex­ist­ing build­ings and those long gone. From the sergeants’ mess (now Samy’s Curry) to the mil­i­tary hos­pi­tal (now Loewen by Dempsey Hill), there is his­tory at ev­ery turn.

Once you’ve had your fill of the past, it’s time to turn to hungers present! There are restaurants, cafés and bars aplenty at Dempsey, and some­thing de­li­cious to eat, drink or nib­ble at ev­ery hour of the day. Try the orig­i­nal black pep­per crab at Long Beach or cool off with a cock­tail at ver­dant The Green Door. It’s a great fam­ily des­ti­na­tion too, with lots of ac­tiv­i­ties for the kids. Drop them off for a swim class at Swish! Swimming or hone their art skills at Im­pres­sions Art Stu­dio, while you browse the fur­ni­ture shops and gal­leries. Then you can all dig in to burg­ers and shakes at Road­house, Ital­ian fare at pop­u­lar La For­ketta or any of the many fam­i­lyfriendly restos.

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