If Clarke Quay is the party central of Singapore, then the Ann Siang and Club Street area is its cool, younger cousin—fully charged with an electrifying atmosphere after dark and a favourite with night owls and nightlife lovers in the know.

One of the neighbourhood’s most distinct features is the rows of restored shophouses that line its streets. Here, you’ll find yourself at the crossroads of the old and new, as the district’s rich history merges seamlessly with trendy shopping and dining options.

Night shot of shophouses along Ann Siang and Club Street

Heritage and history
Daytime shot of the establishments in Ann Siang Hill

For a taste of the district’s heritage, take a stroll down Chinatown’s pioneer’s trail in Ann Siang Hill and Telok Ayer Green. The district was once a predominantly Chinese migrant settlement, and you’re bound to discover hints of its past as you explore the neighbourhood.

Meander through the colourful shophouses of the enclave, past iconic landmarks such as the old well on Ann Siang Hill and historical places of worship such as Al-Abrar Mosque, which has been standing since the mid-1850s.

Visitors can also head to the Singapore Musical Box Museum, tucked away on Telok Ayer Street. The museum’s home to over 40 antique musical boxes, and is housed in the Thian Hock Keng Temple Annexe, the first educational institution set up by the Chinese community in Singapore in 1849.

Be sure to also keep an eye out for the house clan associations in the area, such as the Singapore Hokkien Huay Kuan on Telok Ayer Street, which were first set up by migrants as cultural collectives, and are rich in ethnic history.

Eat, drink and be merry
Array of dishes and drinks served at The Coconut Club.

The main draw of the Ann Siang and Club Street area has to be its vibrant, hip dining and drinking scene. Meat lovers should swing by Yen Yakiniku, where you can feast on farm-to-table cuts of Japanese wagyu or American and Australian grass-fed steaks.

Alternatively, head down the street for no-frills local flavour such as nasi lemak (fragrant rice dish cooked in coconut milk and pandan leaf, accompanied by an array of side dishes like omelette, fried fish and anchovies) and otak-otak (spicy grilled fishcake) at The Coconut Club, which was awarded the Michelin Bib Gourmand in 2018.

For a tantalising menu of Asian food with an innovative twist, hop over to Ding Dong where you can chow down on dishes such as rendang beef brisket buns and lobster tail in tom yum broth.

If you’re in the mood for dessert, be sure to drop by PS Café—a favourite haunt of locals with a sweet tooth, this charming establishment serves up a range of Western comfort food and confectionaries (be sure to try their decadent double chocolate blackout cake).

People enjoying drinks at the Native Cocktail bar at Amoy Street, Telok Ayer.

Ann Siang Road and Club Street are buzzing with energy come nightfall—the roads are closed to traffic on Friday and Saturday evenings, with crowds (and maybe even drinks) spilling out onto the streets.

Swing by Native, an award-winning cocktail bar (on Asia’s Best Bar list) that serves up concoctions made with ingredients sourced from Singapore and across the region, like pineapple arrack and goat’s milk from Hay Dairies. Or, tuck into classic Brit bar nosh and tipples at Oxwell & Co, which serves up drinks garnished with herbs from its garden.

Shop at niche boutiques
Flatlay of menswear products in a suitcase featuring local designer brands against a neutral background.

If you’re looking for a spot of retail therapy, the area also offers an eclectic selection of shopping options.

Fitness fanatics can head to Lorna Jane to pick out spunky new athletic wear before heading to Level Gym or SLAP Dance Studio a brisk 10-minute walk away to clock in some cardio. Both offer trial and one-off sessions you can easily sign up for.

Dapper gents can make an appointment at Truefitt & Hill for their old-school barber shop grooming packages. Then, try Q Menswear and Ed Et Al on Telok Ayer Street for bespoke fashion items and shoes respectively that will keep you at your most stylish.

You can also stop by Aster by Kyra for something traditional—this niche store carries vibrant Peranakan (Straits-born people of Chinese and Malay/Indonesian heritage) floor and wall tiles, which make for unconventional, authentic souvenirs.

Cosy up
The exterior of The Scarlet Singapore located along shophouses on Erskine Road

After a long day of shopping, dining and exploring, grab some shut-eye and good old R&R at any of the accommodation options in the Ann Siang and Club Street area.

Check in to backpacker hostels in the area, such as 5footway.inn at Ann Siang, if you’re looking to travel on a budget (with the bonus option of socialising with fellow travellers).

Book a stay at one of the area’s boutique hotels. The Scarlet Singapore, for instance, occupies a row of pre-war shophouses on Erskine Road and boasts a suite with an outdoor jacuzzi where you can unwind.