Be a tourist in your own country

Amidst the dazzling modern malls, it’s easy to miss the beautiful public art strewn across Orchard Road. Follow this trail we've come up with and find a renewed appreciation for Singapore’s glitziest shopping street.

Location: Outside Regent Hotel

Begin your cultural journey right outside Regent Hotel. There, you’ll find renowned sculptor Stephanie Scuris’ Harmony Fountain, which takes on a multicoloured hue come nighttime. 1 Cuscaden Rd.

Pitstop: Manhattan Bar

If you’re near Regent at night, head on in and up to Manhattan Bar. This New York-styled bar has been deemed Asia’s best cocktail establishment. Have one of their barrel-aged concoctions; you won’t regret it. 2/F, Regent Hotel

Location: Outside The St. Regis Singapore

A short hop away along Tanglin Road is The St. Regis Singapore, where three different artworks await. There’s the buxom Reclining Woman by Fernando Botero, the cuddly Dragon-Riding Bodhisattva by Li Chen, and the intriguing Sense Surround by local artist Anthony Poon. Spot them all. 29 Tanglin Rd.

Location: Outside Orchard Parade Hotel

Continue down the road to Orchard Parade Hotel, where the late Cultural Medallion holder Ng Eng Teng’s Mother & Child is perched. The Cultural Medallion is Singapore’s highest arts accolade. 1 Tanglin Rd.

Pitstop: Benjamin Browns

Ice-cream breaks are always fun, but take it to the next level over at Benjamin Browns, where over-the-top milkshakes and other desserts will ensure your day is filled with a sugary high. #01-20/21 Forum the Shopping Mall, 583 Orchard Rd.

Location: Outside Hilton Singapore

Yes, in front of yet another hotel stands another set of art pieces. Seemingly guarding the main entrance of Hilton Singapore are sculptures Wei Chi Jing De & Qin Shu Bao by Aw Eng Kwang. Peer above the hotel’s entrance and you’ll also see the massive Eulogy to Singapore by Gerard D’Alton Henderson. 581 Orchard Rd.

Location: Outside Four Seasons Hotel Singapore

Take a slight detour away from the main Orchard street, through Hilton Singapore’s linkway, and you’ll find yourself near Four Seasons Hotel Singapore. Look out for the leaf-like sculpture—it’s Sun Yu-li’s Vitality. Soothing. 190 Orchard Blvd.

Pitstop: Privé Orchard

One of the best things to do along Singapore’s busiest street is to people watch. At al fresco diner and bar Privé Orchard, a row of seats face outward so you can do just that while enjoying a cold one. If you’d rather some privacy for lunch or dinner, have a seat further inside. 501 Orchard Rd.

Location: Outside ION Orchard

It’s time to head over to the main shopping belt. Right above Orchard MRT station and outside the shimmering ION Orchard mall, is Nutmeg & Mace by Kumari Nahappan. Sometimes mistaken as an avocado, the nutmeg sculpture is actually an ode to the area’s once humble origins as an area filled with fruit orchards, nutmeg plantations and pepper farms. 2 Orchard Turn

Location: Outside Ngee Ann City

Further up main street is the grand dame of the shopping district, Ngee Ann City. Out at the complex’s civic plaza events space is a fountain flanked by Professor Liu Ji Lin’s Harmony. Take a seat at one of the many benches near here and take in the bustling city vibe. 391 Orchard Rd.

Location: Outside Paragon

Across the road outside upscale shopping mall Paragon, take your time to check out more of Sun Yu-li’s artworks—Celebrations, Endearment, Courtship, Development, Friendship and Relaxation. See if you can tell which sculpture is which. 290 Orchard Rd.

Pitstop: Emerald Hill

Between nearby Midpoint Orchard building and The Centrepoint mall, is an alleyway filled with some of Orchard’s coolest bars and restaurants. Head into casual dive bars like Acid and Alley Bar, as well as a place simply called No. 5 Emerald Hill, that serves up affordable martinis and mouthwatering local fusion bar bites.

Location: Winsland House II courtyard

Take a jaunt further down Orchard Road, past Somerset MRT station, and you’ll find commercial building Winsland House II. It’s worth locating this place and take a picture with renowned pop artist Robert Indiana’s famed LOVE sculpture. 3 Killiney Rd.

Pitstop: Kim Dae Mun Korean Food

A favourite haunt for locals both during lunch and dinner, you’ll be hard pressed to find a seat at this home-styled Korean diner—but it’s worth it if you do. Order up a hot plate of spicy shredded chicken, warm kimchi soup or fried saba fish, and pair it with a cold bottle of Hite for a comforting meal to end the day. #01-03 Concorde Hotel Singapore, 100 Orchard Rd.