There's a hill behind Orchard Road, a hill with private housing units, pubs, bars, and restaurants. Well it is Emerald Hill (Chinese: 翡翠山), it is a well-known place to hangout in among foreigners and youngsters in Singapore. It used to be the home area for the Peranakan, who is the city's wealthy community. William Cuppage is the original owner, who rose from being a postal clerk to acting Postmaster General in the 1840s. In 1837, he leased Emerald Hill and secured a permanent grant for his nutmeg plantation in 1845 which later failed in the 1860s due to disease.
I like to visit the place during daytime as it is peaceful and thus an ideal place for relaxation. At the same time, it’s an enjoyable time to shoot in Emerald Hill as one can get to shoot Chinese Baroque architecture (doors, windows, gates etc.), friendly residents and kids (there’s an international school) and trust me they are more than willing for someone to take photos of them.
If you visit the place at night, it would be a heaven for beer, supper, and performances by live bands. A very good hangout place if you are looking for fun yet not an overly crowded place.
So add that into your consideration for a visit?