Despite being known as one of Singapore's most bustling retail hubs, Orchard Road shouldn’t be looked over when it comes to a night out. Start at the Tanglin end of Orchard Road where it’s quieter and a little more laid-back. Here, you’ll find outdoor cafés where you can start your evening with a Japanese or Italian dinner. Then there’s Horse’s Mouth, the secret cocktail bar with an entrance hidden behind a curtain, where you’ll slip underground and sip signature libations while feeling like you’re in a spy movie!
Walk off dinner and cocktails and head towards Wheelock Place and Scotts Road, where the malls become busier and the streets more crowded. This is the ideal place to people-watch, as it’s one of the city’s most-used intersections. Have a glass of wine at Wheelock Place, or find a table facing the street at the bar on the corner of Scotts Road and Orchard Road. You’ll love the diverse mix of people who walk past: trendy teenagers, families, joggers out for an evening run – and of course, the serious shoppers laden with bags.
Speaking of shopping, you might want to duck into Ion Orchard for a little retail therapy before moving on to the area around Somerset MRT station. This unique area is home to malls, restaurants and a stretch of shophouse restaurants and bars on Killiney Road. It also houses a great selection of Japanese restaurants and bars, including award-winning Japanese craft beer at JiBiru, and sake bars where you can sample a range of nibbles along with your drinks.
Very close to Somerset MRT station is a charming enclave known as Emerald Hill. This conservation area used to be a Peranakan (Straits Chinese) residential area, and the gorgeous mansions and houses are still standing on either side of cobblestoned streets. The shophouses have been converted into popular bars today, most of them casual and relaxed, with live music and great happy hour deals. Despite the very modern surroundings of Orchard Road, you’ll feel like you’ve stepped into a different world in Emerald Hill when you sit at an outdoor table with a beer, looking at the French windowed-shophouses, lush greenery, and Chinese lanterns around you.
A short walk away is Cuppage Terrace, located just off Orchard Road. This charming collection of bars and restaurants features a central al fresco seating area that's covered by a high awning – so it's a great spot to take shelter in if rain strikes without warning! If you're in a wine and cheese sort of mood, you'll be impressed with the wide selection and reasonable prices offered at Wine Connection. Cuppage Terrace also features a Harry's Bar, one of Singapore's most popular casual drinking and dining chains.
Cross the street and you'll find yourself at KPO, which stands for Killiney Post Office – a unique themed bar located right next door to one of Singapore’s most central post offices. Located in convenient proximity to Dhoby Ghaut MRT, this popular spot for afterwork drinks is an ideal place to chill at the end of a night out on Orchard Road.