Things to Do in Dempsey Hill
Dempsey Hill, Singapore - Complete Travel Guide
Top Things to Do in Dempsey Hill
Restaurant hopping among the converted barracks
These restored colonial buildings house excellent restaurants ranging from casual bistros to fine dining establishments. You might move from a wine bar in one building to a rooftop restaurant in another. Perfect setup. The whole layout encourages this kind of leisurely exploration between converted military structures.
Antique and home decor shopping
Several buildings house antique dealers and home furnishing stores worth browsing even if you're not buying. The shops specialize in Asian antiques, vintage furniture, and unique home accessories. You won't find this stuff in typical shopping centers—much more character here than mall shopping.
Weekend brunch culture
Weekend brunches have become Dempsey Hill's signature draw. Families settle in for hours with newspapers and multiple courses, treating the outdoor seating areas under mature trees like resort dining. Much more relaxed. The pace here encourages lingering over coffee and conversation instead of rushing through meals.
Evening drinks with a relaxed atmosphere
After-work drinks transform the area as sun goes down. Several wine bars and cocktail spots offer outdoor seating that attracts the expat crowd looking for conversation-friendly alternatives to Singapore's busier nightlife areas. The setting encourages actual talking. You'll find more meaningful conversations here than in crowded Clarke Quay or Boat Quay venues.
Photography walks through the historic architecture
Black-and-white colonial buildings and mature trees create genuinely photogenic scenes throughout this compact area. The architecture tells Singapore's colonial story in a more intimate setting than typical heritage trails. Small enough scale. You can capture the whole character of the place during a focused walk between the converted military buildings.