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Enjoy a Friendly Chat Over a Cuppa at the Best Dempsey Cafe

Chloe Lim· Food & Lifestyle Editor· Updated 26 May 2026
Enjoy a Friendly Chat Over a Cuppa at the Best Dempsey Cafe

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What is it about Dempsey Hill that makes it a perfect spot for a cafe?

Dempsey Hill exudes a charming blend of rustic elegance and lush greenery, making it the perfect spot for a relaxing café experience. Once a colonial barracks, this tranquil enclave has transformed into a lifestyle destination where time seems to slow down amid heritage architecture and nature’s embrace. Whether you’re catching up with friends or enjoying a quiet solo coffee, Dempsey Hill’s cosy cafés offer the ideal escape from the city buzz—complete with aromatic brews, artisanal treats, and a warm, laid-back vibe.

1

AIR CCCC

Website

https://aircccc.com/

Contact Details

+65 8228 1528 bookings@aircccc.com

Menu

Granola with Annie’s Yogurt, Potato Croquette from Scratch, Chocolate Babka

Nestled in the heart of Dempsey Hill, AIR CCCC is a modern Dempsey cafe that combines creative aesthetics with warm, home-like charm. This café offers food lovers an escape from the city, surrounded by lush greenery and calming interiors. Known for its coffee and fresh bakes, this outlet also serves delicious desserts and brunches that highlight quality produce from local collaborations. Whether you’re meeting friends for a catch-up or simply want to unwind at Dempsey, AIR CCCC delivers a memorable dining experience. Their menu balances classics and creative twists, from smoked chicken toast or housemade kimchi grilled cheese for breakfast to a melt-in-your-mouth chocolate babka. A true haven for the community, it’s a must-visit spot in Singapore for great vibes, great coffee, and great conversations.

2

Da Paolo Dempsey

Website

https://www.dapaolo.com.sg/dempsey

Contact Details

+65 6261 3128 enquiry@dapaolo.com.sg

Menu

Burrata Pugliese, Spaghetti alla Nerano, Lemon Tart

Located in the lush landscape of Dempsey Hill, Da Paolo Dempsey is a stylish Italian dining destination that celebrates the world of authentic flavours. Its menu is a perfect collection of hearty dishes and desserts, each crafted with care and passion. The café’s retail section allows you to take home some of their gourmet products, too. Food lovers in Singapore adore this outlet for its blend of traditional recipes and modern twists. Expect portions that satisfy and cocktails that delight, all served in an inviting seating area that’s ideal for any occasion. Whether it’s a family dinner, a weekend brunch, or simply a coffee catch-up at Dempsey, Da Paolo promises an unforgettable dining experience that’s both elegant and comforting.

3

Jean-Georges

Website

https://www.jean-georges.com/

Contact Details

+65 1800 304 5588

Menu

Gourmet Chicken Dishes, Signature Pork Mains, Innovative Desserts

Jean-Georges brings a taste of the world to the Dempsey Hill community, offering refined dining with a global touch. This cafe-restaurant hybrid is part of an exclusive collection of cafes in Singapore that redefine casual luxury. Expect meticulously crafted plates, seasonal produce, and a curated menu that balances classics with creative flair. The ambience is sleek yet comfortable, perfect for friends, couples, or business collaborations. With lush greenery surrounding this outlet, every meal here feels like a mini escape from the bustle of the city. Pair your meal with an artisanal coffee or a signature cocktail for the ultimate dining experience at Dempsey.

4

PS.Cafe – Chopsuey Cafe

Website

https://www.pscafe.com/

Contact Details

+65 6708 9288 +65 6271 7288 concierge@pscafe.com

Menu

Kung Pao Chicken, Honey Ginger Chicken, Beef Cheek Rendang

No guide to Dempsey cafes is complete without mentioning PS.Cafe – Chopsuey Cafe. This iconic outlet blends Asian-inspired dishes with Western classics, offering food lovers a wide variety of vibrant plates. The menu is filled with bold flavours: think chilli, pork, and chicken delights, perfectly complemented by their legendary chocolate desserts. The lush greenery of Dempsey Hill provides a stunning backdrop for a laid-back brunch or evening dinner with friends. Whether you’re celebrating a special occasion or just catching up over coffee, this dining spot is as stylish as it is welcoming. With generous portions and a thoughtful range of options, it’s a place where you can relax, indulge, and enjoy everything Singapore café culture has to offer.

5

The Dempsey Project

Website

https://thedempseyproject.com/

Contact Details

+65 6475 2005 contact@thedempseyproject.com

Menu

Cinnamon Brioche French Toast, Eggs Florentine, Ri’s Mango Coconut Chia Pudding

The Dempsey Project is a cornerstone of the Dempsey Hill community, bringing together food, retail, and a sense of connection in one vibrant outlet. Its menu features a range of international dishes and healthy options, perfect for those who love to explore new flavours. With its inviting seating, friendly service, and emphasis on fresh produce, this café offers one of the best dining experiences in Singapore. Whether you’re sipping coffee or enjoying a wholesome brunch with friends, you’ll feel at home at this destination cafe. The retail section adds another dimension, allowing you to bring a piece of Dempsey Hill home—from gourmet sauces to artisan chocolate and coffee blends. Truly, The Dempsey Project is a must-visit spot for food lovers seeking authenticity, flavour, and community.

6

FAQs

1. How do I get to the Dempsey cafes?

You can take a shuttle bus service from Orchard or Holland Village directly to Dempsey Hill, making it an easy escape from the city bustle.

2. Which Dempsey cafe is best for brunch?

The Dempsey Project, Puzzle Coffee, and PS.Cafe are top choices for hearty brunches with excellent coffee and desserts.

3. Are these cafes family-friendly?

Absolutely. Most cafes at Dempsey Hill offer kid-friendly menus, spacious seating, and a relaxed atmosphere perfect for the whole family.

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Chloe Lim

About the author

Chloe Lim · Food & Lifestyle Editor

Chloe covers Singapore's dining, beauty, and lifestyle scene — eating and testing her way across the island so her picks are ones she'd send a friend to.