Dempsey & Holland Village

Dempsey Hill and Holland Village anchor Singapore's most established expat drinking corridor — a leafy, low-rise belt of former British military barracks, independent restaurants, and destination bars that sits just west of the Botanic Gardens and Orchard Road. The two areas have distinct personalities but serve a similar crowd: well-travelled professionals, long-term residents, and weekend visitors who want quality in comfortable, unhurried surroundings. Dempsey Hill is the more distinctive of the two. The cluster of converted colonial barracks set among mature rain trees has become home to some of Singapore's most interesting independent food and drink venues, including a brewpub with its own tanks visible from the bar — a rarity in land-scarce Singapore. The car-dependent nature of Dempsey, which has no MRT station, has if anything helped preserve its neighbourhood character: this is not a destination for the rushed or the casual. Holland Village, a short drive or bus ride away, is older and more layered — Singapore's original expat village, built around a small commercial strip that has somehow resisted full gentrification. The bar scene here is more varied, ranging from long-standing neighbourhood institutions to newer craft-focused openings in the surrounding streets of Lorong Mambong and Jalan Merah Saga. For craft beer drinkers staying in or around Orchard, Dempsey and Holland Village offer a more relaxed, residential alternative to the CBD strip.