You’ve probably heard about Orchard Road, Sentosa Island, Marina Bay and all the other must-visit attractions in Singapore. But save some time for Dempsey Hill — a lesser-known locale that’s home to luxury shops and stellar dining options.

A nutmeg plantation in the 1850s and the former site of a British colonial barracks for over a century, Dempsey Hill has been through several transformations, which you can learn about with a stroll along its walking trails.

Redeveloped in 2007, this heritage site is now an idyllic lifestyle destination, filled with charming shops and restaurants.

Retail and dining
Closeup shot of a dish served at COMO Dempsey

Located atop Dempsey Hill, COMO Dempsey is a hip lifestyle enclave that houses a variety of original and innovative dining places and concept stores.

Candlenut—the world’s first Michelin-starred Peranakan* restaurant—is one such tenant. Founded by homegrown chef Malcolm Lee, this 4,262-square-foot restaurant boasts a 92-seat capacity and an al fresco dining area. Its interiors—designed by renowned architect Paola Navone—combine modern design with touches of Peranakan heritage.

For more Michelin fare, be sure to reserve a table at Burnt Ends, where you can savour Australian-style barbeque and juicy cuts of meat by chef-owner Dave Pynt.

Other dining destinations at COMO Dempsey include Ippoh Tempura Bar – which serves up Japanese fare hailing from Osaka– and Dempsey Cookhouse & Bar by Michelin-starred chef Jean-Georges Vongerichten.

A variety of swanky dining and nightlife options abound all around Dempsey Hill. Check out Red Dot Brewhouse for a hearty menu of steaks and beers or get your fill of local cuisine, at the famed Long Beach Seafood Restaurant, and Samy’s Curry.

If you enjoy Sunday brunch and going green, experience Open Farm Community’s refreshing farm-to-table concept. The latter is helmed by world-renowned chef Ryan Clift, with dishes created from locally farmed ingredients.

*The term is an Indonesian/Malay word that means “local born”, which generally refers to people of Chinese and Malay/Indonesian heritage.

Fun, fashion and family time
Wideshot of Farmers Market at Loewen Gardens.

Plan an enriching weekend for the whole family at Loewen by Dempsey Hill, where you can choose from a multitude of activities for both kids and adults.

Pick up gymnastics with the classes at The Yard,  or get your heart rate pumping with a high intensity interval training session at Core Collective Dempsey.

Parents visiting with their little ones should certainly drop by The Museum of Ice Cream, a pastel-hued wonderland with 14 ice cream-themed attractions like the Sprinkle Pool.

If you’re in the mood for some pampering, be sure to drop by Trimmings when you’re done with your shopping spree, and indulge in a pedicure or massage. There’s even something for your furry friends — check them in to the Wagington Luxury Pet Hotel, which boasts spa service  and day carefor your pooch or cat.

Fashionistas looking for inspiration should look no further than Dover Street Market Singapore. Founded by Commes des Garçons designer Rei Kawakubo, this legendary retailer has a cult following for its line-up of high fashion apparel. 

To get to Dempsey Hill, hop on a shuttle bus at their many pick-up points. View the shuttle bus schedule, and visit Dempsey Hill’s official website for more information.