You probably already know some of the eclectic boutiques, eateries and bars dotted around tranquil Dempsey Hill. If you’ve been living in Singapore for awhile, you might even know that its sprawling black-and-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 family friendly restos.
A series of walking trails take in all the Dempsey hot spots:
- Nature-Heritage Trail – perfect for families and history buffs who like to get out in the open air and explore.
- Epicurean Trail – if food is your thing you’ll be spoilt for choice with international and local restaurants, gourmet grocers and more.
- City-Dweller Trail – from brunch and boutiques to beauty treatments and antiques, this trail takes in the best of Dempsey’s little pleasures.
A free shuttle bus picks up passengers at Wheelock Place, Botanic Gardens (Tanglin Gate and Nassim Gate) and Holland Road Shopping Centre. Full details at dempseyhill.com.
For more helpful tips, head to the Living in Singapore section!