With its prime real estate right outside the city and idyllic low-rise colonial buildings, Dempsey Hill feels like a little slice of old-school heaven on earth. And it’s in this bohemian-esque hideout that you’ll find some of Singapore’s best restaurants. So, grab a friend and spend a day trying the delicious food at these Dempsey Hill restaurants.

Dempsey and Blu Kouzina make a perfect match. The former’s grassy gardens and this restaurant’s Greek greenhouse setting make for a meal that feels straight out of Mamma Mia. 

Once you’ve sat yourself down at the genuine Greek dining tables, order some Melitzanosalata eggplant salad for a hit of that lightly smoked, herbal flavour profile that has come to be synonymous with Athens.

Then, treat yourself to the Souvlaki Me Pita, an authentic grilled beef pita stuffed with tomatoes, tzatziki, and fragrant spices. The dish has a side of fries, so remember to keep enough space in your tummy. I recommend pairing your pita with the Taramasalata White Cod Roe Dip, whose tangy and salty flavours will seep into your pita to elevate its taste.

For dessert, finish up with some Baklava. Unlike its Turkish cousin, this Greek pastry comes in a more dense, cylindrical form that’s loaded with sweet walnuts and almonds. It’s a super-indulgent way to end your meal.

📍 Address: 10 Dempsey Road, #01-20, Singapore 247700
⏰ Opening hours: 11:30am – 2:30pm, 5:30pm – 9:30pm daily
📞 Contact: 9710 8303
🍴 Halal status: Halal ingredients
🌐 Website: blukouzina.com/restaurants/dempsey

Candlenut isn’t just the only Michelin-starred Peranakan restaurant in Dempsey Hill — it’s, in fact, the world’s first such restaurant. The fame didn’t come easy as the cuisine, known for its nutty and fragrant flavours, requires meticulous preparation.

For one, the Chap-Chye is slow-cooked to the point where its cabbage turns into a melt-in-your-mouth goodness. The Snake River Farm Kurobuta Pork Neck Satay and Udang Sambal Petai are must-tries if you’re big on meat and seafood. 

But it’s the restaurant’s Ah-Ma-Kase (like omakase, but different) menu, which rotates monthly, that’s the real deal. The current lunch menu includes highlights like Charcoal Grilled Bangus (milkfish) Belly Satay and Tau Yu Bak (slow-cooked iberico pork jowl). If you’re heading down for dinner, be sure to try Yeye’s Crab Curry and the decadent Orange Sugee Cake.

📍 Address: 17A Dempsey Road, Singapore 249676
⏰ Opening hours: 12pm – 3pm, 6pm – 10pm daily
📞 Contact: 1800 304 2288
🍴 Halal status: Not halal
🌐 Website: comodempsey.sg/restaurant/candlenut

Since 1988, Margarita’s has attracted diners in droves not just for its namesake cocktail but rather for its timeless command of rugged, rustic Mexican fare. From the intense, chunky Pico De Gallos to Queso Fundido bowls made from low-fat and creamy Mexican Oaxaco cheese, every dish here transports your taste buds from Dempsey Hill to Mexico.

To ensure that it continues to serve customers authentic flavours, many of Margarita’s ingredients are imported straight from the land of the Aztecs. If you’ve ever wanted to sample the complex flavours of a chocolate-spiked Mole Poblano chicken, this is one of the few places in Singapore that will treat you right. And to top it off, you’ll be able to end your meal with one of their famous Kahlua Tiramisus that are rich enough to beat any mousse in town. ¡Buen provecho!

📍 Address: 11 Dempsey Road, Singapore 249673
⏰ Opening hours: 11:30am – 10:30pm daily
📞 Contact: 6471 3228
🍴 Halal status: Not halal
🌐 Website: margaritasrestaurante.com

Samy’s Curry attracts hungry diners all day, and for a good reason — which other Dempsey Hill restaurant can boast free-flow briyani? Not just that, but many of the dishes here are spiced liberally with a secret spice blend that’s remained the same since 1960. The result is an explosion of flavours in your mouth. For maximum South Indian vibes, meals here are served on banana leaves, too.

Those with a big appetite can’t afford to miss the restaurant’s legendary Fish Head Curry, known for its tanginess and spiciness that pervades throughout the dish.

📍 Address: 25 Dempsey Road, Singapore 249670
⏰ Opening hours: Wed to Mon 11am – 3pm, 6pm – 10pm
📞 Contact: 6472 2080
🍴 Halal status: Muslim-owned
🌐 Website: samyscurry.com 

Be ready to feel enchanted from the moment you set foot in the compound of this 40,000-square-foot Dempsey Hill restaurant. Once you’re in, you’ll be greeted by the tantalising smell of various dishes wafting from the restaurant’s open kitchen.

Crack open the menu and order the Whole Coral Grouper, served in a generous sharing plate for 2. The sustainably harvested fish not only comes fresh and packed with its wild flavour but is also accented further by the Beurre Blanc sauce. This special sauce is made from emulsified portions of the grouper to bring out the velvety and earthy textures of the dish.

In addition, Air CCCC’s menu features an array of unique eats made from regionally sourced dishes. You’ll know what I mean when you try the Grilled Kampong Chicken made with chimichurri and the Cocoa Husk & Brown Butter Ice Cream, which caught my attention for using cocoa husk instead of cocoa beans.

📍 Address: 25B Dempsey Road, Singapore 249918
⏰ Opening hours: Wed and Thu, 11:15am – 3pm, 5:30pm – 11pm | Fri, 8am – 3pm, 5:30 – 11pm | Sat and Sun, 8am – 3pm, 5pm – 11pm
📞 Contact: 8228 1528
🍴 Halal status: Not halal
🌐 Website: aircccc.com

Ps. Cafe is a cosy chain that’s been a mainstay of Singapore’s cafe scene since 1999, and its Dempsey branch brings its hearty, simple joys to a brand new canvas.

Every PS. Cafe is decorated differently to get the most out of its environment, and its Dempsey Hill restauarant is no exception. This outlet offers an outdoor seating area that overlooks the surrounding forest. The views of uninterrupted greenery are a tonic for the mind and a rarity in an otherwise concrete jungle. 

Of course, you’ll find all the PS. Cafe classics here, like their classic Mushroom Soup, made with that textured, mellow flavour that you can only get from wild mushrooms. Once you’ve slurped your bowl clean, don’t forget to order some Crab Tarts. Each one is absolutely loaded with succulent crab meat that’s already de-shelled so you can dig in straight.

The menu also has a few goodies you can’t get at any of its other branches, including a duck confit that pairs a fall-off-the-bone tenderness with the rich, oily flavours innate to duck meat.

📍 Address: 28B Harding Road, Singapore 249549
⏰ Opening hours: Sun to Thu, 8am – 10pm| Fri and Sat, 8am – 10:30pm
📞 Contact: 6708 9288
🍴 Halal status: Not halal
🌐 Website: pscafe.com 

Even though Da Paolo outlets are peppered across Singapore, its Dempsey branch offers several signatures that you’ll not find elsewhere. These include pizzas made from a unique blend of semolina flour, giving the slices a delicious crackling sound when bitten.

True to its Italian roots, the food here is steeped in flavour. Choose from options like Diavola, the classic Margherita, and even a quirky one called the 8 Cheese & Dark Chocolate, which contains 68% Valrhona dark chocolate. Some non-pizza highlights include Sweet Corn Lobster Risotto and Grilled Lamb Rack.

No matter what you’re eating, you’re bound to leave Da Paolo with a full stomach and the moon in your eye like a big pizza pie (that’s amore!)

📍 Address: #01-13 Dempsey Road, Blk 8, Singapore 247696
⏰ Opening hours: Sun to Thurs, 8am – 11:30pm | Fri and Sat, 8am – 12am
📞 Contact: 6261 3128
🍴 Halal status: Not halal
🌐 Website: dapaolo.com.sg/dempsey

Jumbo Seafood has truly mastered the Chilli Crab and propelled the humble dish to international fame, so it’s no surprise that it’s one of the most-visited Dempsey Hill restaurants.

From Black Pepper to Stir Fried Kum Hiong, the chefs at Jumbo’s Dempsey branch know enough ways to prepare a crab to impress any critical aficionado. But personally, I’m a fan of the individually de-shelled, addictively umami Golden Salted Egg Prawns. They’re basted in lots of creamy batter, so that every bite bursts with runny salted egg goodness that gives way to the sweet flavour of the restaurant’s carefully-selected prawns. Make sure you have a tissue ready for those prawn juices.

📍 Address: 11 Dempsey Road, #01-16, Singapore 249673
⏰ Opening hours: 11:30am – 2:30pm, 5:30pm – 10:30pm daily
📞 Contact: 6479 3435
🍴 Halal status: Not halal
🌐 Website: jumboseafood.com.sg

Part restaurant, part workshop, and full of chocolatey goodness, Mr Bucket Chocolaterie is a one-stop destination for all things artisan chocolate. Every bar, slab, and dragee here is made from sustainably sourced cocoa from small regional farmers and made in the workshop’s open kitchen.

Treat yourself to one of the restaurant’s bean-to-bar tasting sets, which start with a Cacao Bean Dark Chocolate Dragee that looks like it’s been plucked straight out of the farm. The dragee is equal parts velvety and crunchy and melts in your mouth effortlessly.

The rest of the items in the set are equally impressive, with a 64% chocolate passionfruit sable that lends them a zesty and luxuriously silky experience.

Once you’ve exercised your sweet tooth, check out the restaurant’s collaboration menu with neighbouring cafe Yoshoku. Yoshoku follows a similar farm-to-table ingredient philosophy, so this is your chance to finish off your meal with exquisite bites like Norweigan Salmon Aburi and Negi Miso Chicken.

📍 Address: 13 Dempsey Road, #01-03/04, Singapore 249674
⏰ Opening hours: Sun to Thu, 11am – 7pm | Fri and Sat, 11am – 10pm
🍴 Halal status: Not halal
🌐 Website:  mrbucket.com.sg

A classic Dempsey Hill restaurant, Rakuichi offers understated Teppanyaki-style eats the whole family can enjoy.

In the spirit of fusion cuisine, there are a few freestyle selections here, too. The Rakuichi Rainbow Maki Roll sees the intense, buttery flavours of a whole soft shell crab tempered by layers of avocado and various sashimi. But if you’re looking for something for the ‘gram, order the Sumiyaki Moriawase, which will have you spinning skewers of specially selected cuts right on top of a brick grill!

📍 Address: 10 Dempsey Road, Singapore 247700
⏰ Opening hours: 11:30am – 2:30pm, 6pm – 10pm daily
📞 Contact: 6474 2143
🍴 Halal status: Not halal
🌐 Website: rakuichi.com.sg

(Featured photo adapted from: Daniel Food Diary, Mr Bucket, Miss Tam Chiak, Thirst Mag)