If Dempsey Hill’s walls could talk, they’d have some pretty wild stories to tell. But since they can’t, the lush lifestyle enclave – better known for its top-tier restaurants and chic boutiques – is leaving the talking to a brand-new immersive audio tour that brings its storied past to life.
Fun fact: Before it became Singapore’s go-to spot for Sunday brunch and boutique shopping, Dempsey Hill had quite the journey. Once romantically called “Mount Harriet” in the mid-1800s, the area later transformed into the Tanglin Barracks, a key military base during Singapore’s colonial era. Soldiers trained, officers strategised, and history unfolded – right where you now sip your artisanal coffee.
With this self-guided tour, you can step back in time and hear the untold stories that shaped Dempsey Hill’s evolution. The 40-minute experience, created in collaboration with Klook, Dempsey Hill, and Cinewav, brings the past to life with rich storytelling.
One of the best things about this tour? No rushing. You can pause, wander, and soak in the surroundings at your leisure. Spot the remnants of colonial architecture, find hidden corners filled with history, and perhaps stop for a quick pastry or cocktail break whenever the mood strikes.
Tickets are priced at $25 per pop. Book your ticket on Klook, grab your headphones, and take a walk through time.
HAVE YOU HEARD?
5 cheapest, less-frequented places in Japan with return flights from Singapore under $511
Kampong Gelam Ramadan Bazaar 2025 returns for 35 days this February
Coldplay just released a music video – and it was filmed right here in Singapore