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Things to do in Singapore: Guide to the Dempsey Hill cluster

Exploring the verdant grounds of Dempsey Hill, it’s hard not to notice the tranquillity and old world charm in stark contrast to the modern Singapore! Wandering past the colonial buildings reveals glimpses of the rich history that dates back to the1860s.

In less than two centuries,this charming enclave has transformed from a nutmeg plantation, to military headquarters for British soldiers, to the quaint lifestyle, art and culinary enclave it is today. That’s impressive!

Once you’re done meandering through the buildings and have soaked up all the history, you’ll find gourmet grocers, art galleries, antique shops, highly acclaimed restaurants and cafes all waiting for you at the top of The Hill.

What to do in Singapore? What can you do in Dempsey Hill ? 

What else is there?

  • You could road test Dempsey Hill’s Nature-Heritage Trail and uncover the stories and people behind its transformation, as well as discovering the rich heritage and history of the barracks once known as Tanglin Barrack.
  •  For foodies, take the Epicurean Trail to discover heritage food and iconic dishes that put Singapore on the culinary world map. Spice up your dining experience and find out the inspiration behind Samy’s Curry, to Long Beach Seafood’s famous black pepper crab, and JUMBO Seafood’s award winning chilli crab. 
  • Or, try out the City Dwellers Trail. Start with a brunch at Jones the Grocer , followed by a pampering massage at award winning spa, HOUSE, then have a leisure stroll along the art galleries and antique stores.  End the day and dine at Michelin-starred Chef restaurant, La Ventana or award winning restaurant, The Disgruntled Chef.
  • For the families: Within the City Dwellers Trail, you will discover more about Loewen by Dempsey Hill , which stands on the site of the former military hospital. Built in the 1870s, these buildings have been restored to their former glory, retaining their architectural heritage and charm. It is now home to an education and lifestyle commune offering learning, enrichment, art, and sports including indoor and outdoor swimming classes for children, as well as premium home furnishings, a chocolatier and even a luxury pet hotel.

There’s sure to be something for everyone at Dempsey Hill!

Psst: there’s also a shuttle bus that picks up passengers from Botanic Gardens if you can’t face walking up Harding Road in the heat!

Head on to our Calendar of Events to check out the Christmas Market by Loewen at Dempsey Hill.