Dempsey, Holland Village, Orchard & Sentosa

Dempsey Hill, Holland Village, and Orchard together form Singapore's most established corridor for well-heeled leisure drinking — a leafy arc running from the colonial barracks of Dempsey through the original expat village of Holland Village and up to the shopping and embassy belt of Orchard Road and Tanglin. Each area has a distinct character, but they share a crowd: long-term residents, well-travelled professionals, and weekend visitors who want quality surroundings and a relaxed pace. Dempsey Hill anchors the western end — a cluster of converted British military barracks set among mature rain trees, home to Singapore's most distinctive brewpub. With no MRT station and a largely car-dependent clientele, Dempsey has preserved an unhurried, destination-visit character that the more accessible parts of the city have long since traded away. Holland Village, a short ride away, is Singapore's original expat neighbourhood — a compact commercial strip that has somehow resisted full gentrification, with a bar and restaurant scene ranging from long-standing local institutions to newer craft-focused openings on Lorong Mambong and Jalan Merah Saga. Orchard Road and the Tanglin belt extend the corridor further east, adding the polished hotel bars, rooftop venues, and upscale craft beer options that serve the area's luxury hotel guests, embassy staff, and Orchard-adjacent residents. The Thomson-East Coast Line at Orchard MRT and the Circle Line at Botanic Gardens knit the area together for those arriving by public transport. Whether you're heading to Dempsey for a long Sunday session or stopping off along Orchard for a post-shopping pint, this corridor offers some of the most comfortable and well-appointed craft beer drinking in Singapore.