Why go?

Celebrated for its sleek skyscrapers and ultra-modern urban initiatives, Singapore’s patchwork of grittier neighbourhoods that reveal the region’s cultural history often escape the spotlight. Away from Orchard Road’s glossy malls and the skyline of Marina Bay, Duxton Hill dines out to its own recipe.

Away from the city-state’s polished touristic realm, Duxton Hill presents Lion City life as intimate, eclectic and steeped in heritage. Formerly a hotbed of vice – its narrow cobbled streets notorious for opium dens and gambling houses - the area has been transformed into one of the city’s most sought-after casual dining destinations. Though small, the neighbourhood packs a punch in flavour, with its colourful shophouses and car-free roads playing host to forward-thinking bars and experimental restaurants helmed by chefs and bartenders hailing from across the globe.

What Duxton lacks in size, it makes up for in character. District boundaries are more guidelines than rules – sure, you’ve got Duxton Hill itself, Duxton Road and Craig Road at the heart of the district, but the Duxton label stretches into surrounding streets, melding with nearby Chinatown, as up-and-coming restaurants, trendy cafés and world-famous cocktail bars share in the glory of the neighbourhood ‘s rising reputation.

What to do

Duxton Hill’s history dates to the mid-19th century, when the land was part of a nutmeg plantation owned by a British colonial administrator. In 1856, the area was auctioned off and quickly leased to wealthy Chinese developers, who transformed it into a bustling district. Under British colonial rule, city districts were created to accommodate different ethnicities migrating to the trading city, including the larger Chinatown district. Duxton Road and the surrounding streets became a warren of opium dens, gambling houses and brothels. By the 1900s, it had earned a nickname, Jinrickisha Place, a reference to the rickshaw pullers who frequented the less reputable establishments. Yet it was here that wealthy Straits Chinese merchants began constructing shophouses with intricate designs, featuring colourful facades, arched windows and decorative motifs, and these remain a defining feature of the streetscape. As Singapore underwent modernisation, Duxton’s gritty past faded and the elegant architecture was recognised for its heritage value. Today, the only sins on show are of a more innocuous nature – a little greedy indulgence in the district’s diverse culinary offerings.

Where to stay

At The Duxton Reserve, no two rooms are the same, but all are sultry and ornate in a nod to Duxton Hill’s insalubrious history. This intimate hotel – one of the smallest in the city – has transformed a row of historic shophouses, maintaining heritage features: swathes of black and gold, opium beds and ample lacquer furnishings. Facilities are limited in such a tight space, but onsite restaurant Chinese Yellow Pot plates up excellent Cantonese food. duxtonreserve.com

For a more conventional city stay, head towards the neighbourhood’s giant Kaws sculpture. It belongs to the 302-key, minimalist Mondrian Singapore, which, alongside its big-name contemporary art collection, houses two restaurants, a cocktail bar and a 24/7 fitness centre, plus a rooftop infinity pool with a view from the top of its glassy tower- block home, complete with Hollywood-inspired pool club. mondrianhotels.com

Where to eat and drink

Start an odyssey into international flavours at Xiao Ya Tou, which creates modish iterations of local favourites – think chilli crab omelette and truffle roast duck. For a Latin American twist, try Araya, where ceviche and grilled meats are menu staples. Just around the corner on Duxton Road, Fung Kee serves Scandinavian-inspired hot dogs; while standing sushi bar Rappu is known for handrolls topped with opulent, ultra-luxe ingredients. xyt.sg arayarestaurant.com rappu.sg

Head to Tamba for Canadian chef Kurt Wagner’s take on West African jollof rice and pepper soup, or Luca Loca for a kaleidoscopic Mexican menu, from tacos to tostadas. Meanwhile, just beyond the trio of Duxton’s main roads, Thevar offers Michelin-starred Indian cuisine. tamba.life super-loco.com thevar.sg

Over on Kadayanallur Street, The Maxwell Food Centre is home to over 100 hawker stalls, including icons like Tian Tian Hainanese Chicken Rice (once frequented by Anthony Bourdain) and Zhen Zhen Porridge. There’s plenty of glitz around too: at one-star Born, located within the former Jinrickisha Station, chef Zor Tan marries French culinary technique with Chinese classics. restaurantborn.com

After dinner, dive into Duxton’s award-winning cocktail scene. Tippling Club is known for boundary-pushing libations; the intimate Sago House on Duxton Hill pours drinks inspired by fresh market finds; and head bartender Erika Fajilagot pairs a 200-strong agave collection with Singaporean ingredients at Cat Bite Club – try the complex, earthy Mango Potato Boom. tipplingclub.com catbiteclub.com

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