Dempsey: old army barracks, three very good lunches

Soldiers drilled on this hill once; the hard manoeuvre now is getting a table.

Book the table first and treat everything else on the hill as optional. Three restaurants, three occasions: Candlenut for visitors you want to show Singapore to, or a family lunch with firm views on Peranakan food; Claudine for an anniversary; The Dempsey Cookhouse & Bar for a mixed group where nobody agrees on anything. The compromise is that Dempsey is spread out and rewards a slow afternoon, so it is a poor fit for a quick lunch between meetings. Leave time to arrive without rushing.

The setting helps. The hill is named after General Sir Miles Dempsey, who led the British Second Army across north-west Europe in 1944 and 1945 and later ran Malaya Command, and Dempsey Road and Dempsey Hill sit on the old Tanglin Barracks, whose garrison buildings now house shops, cafés and restaurants. Old army barracks, now doing long lunches.

Candlenut: for visitors and the family

COMO bills Candlenut as the world’s first Michelin-starred Peranakan restaurant, and the 2026 MICHELIN Guide Singapore lists it with one star. Chef Malcolm Lee cooks traditional Straits Chinese food with an Indonesian touch, in a lofty dining room with bamboo and rattan details. You can order à la carte, with dishes served to share, or take the tasting menu of ten-plus courses that changes with the seasons, nicknamed the Ah-ma-kase (a name that sets a high bar in any family with an actual ah ma at the table).

For visitors from abroad, take the tasting menu and let the kitchen make the case. For a family lunch, go à la carte, so everyone can argue over the same plates.

Claudine: the anniversary

Julien Royer, the chef behind Odette, named this neo-brasserie on Harding Road after his mother. It is a converted 1930s chapel with an open kitchen at one end and a bar at the other, sage-green velvet banquettes and the chapel’s original stained-glass window above the bar. The menu keeps to French classics such as foie gras terrine, vol-au-vents and soufflé, with plenty of wine by the glass.

There are two settings. The Dining Room serves the classics; La Terrace is a glasshouse with lighter French-inspired plates. For an anniversary or a proposal, the chapel is the reason to come; for a lighter lunch, La Terrace. When you book, name the setting, not just the restaurant.

The Dempsey Cookhouse & Bar: the mixed-group answer

This is Jean-Georges Vongerichten’s Singapore flagship, at COMO Dempsey. His group describes the food as contemporary Asian-inspired European cooking, served from an open kitchen in a room meant for relaxed communal dining, with high ceilings, chequered tiles and set brunch, lunch and dinner menus. It is the easiest of the three for a group with mixed tastes, and Candlenut is its neighbour on Dempsey Road, so you can compare the two before you choose.

If part of your group would rather shop than linger, COMO Dempsey also houses Dover Street Market Singapore: someone browses while the others finish the wine, and nobody has to pretend to enjoy the other half of the afternoon.

Before you go: what’s gone

Older Dempsey guides still circulate with photos of Open Farm Community and Tiong Bahru Bakery Safari. Both closed in January 2026, and Tiong Bahru Bakery no longer lists a Dempsey branch among its locations, so don’t build a plan around either. Confirm the exact venue and seating area, mention dietary needs or an occasion when you book, and take the hill slowly.

A walk around the old barracks before or after is a nice addition, but the meal is the point. Dempsey will still be there for the next lunch.

Good to know Candlenut and The Dempsey Cookhouse & Bar are on Dempsey Road and Claudine is at 39C Harding Road. Book directly through each restaurant and check current menus and prices, which change.

More on the hill, beyond these three…