I’d like to say I’m an outdoorsy person, with hikes being a major part of my itinerary wherever I go. So when I heard Hasbro’s iconic game Monopoly ditching the board and teaming up with award-winning experience company Hidden for the streets with Monopoly: Hidden Singapore, I laced up my trainers and decided to see if I could trade Park Lane for park walks, and actually enjoy the slog.
What is the Monopoly: Hidden Singapore?
Available now for a limited time only, Monopoly: Hidden Singapore is basically an IRL version of the board game, but without the dice and jail time. The first installment is called Love, Lost & Found – a self-guided trail that stitches together tales of romance, heartbreak and human connection. Over about 90 minutes – or two hours if you, like me, get distracted taking photos – the trail transforms the familiar city into a playful, puzzle-packed adventure.
The game runs entirely on WhatsApp, which means no clunky app downloads, and it’s open to both locals and tourists – I tried it on a foreign number and it worked like a charm. Once you’re connected, a chatbot – otherwise known as Void Deck Cat – will appear as your cheeky game master, feeding you puzzles to solve. Each puzzle takes you through historic neighbourhoods, cultural landmarks and overlooked corners of the city.
You’ll get a tote bag with some useful bits, but I’d still pack smart: a fully charged phone, a power bank, a portable fan, comfy shoes and an umbrella for those sudden downpours. Be warned – there are stairs, slopes, and the kind of humidity that leaves you glistening like you’ve just smashed a spin class.
Where is the start?
My Monopoly adventure kicked off at SMU Connexion, where Void Deck Cat sent me on my first quest: to Onalu Bagel Haús. Here, I picked up a utility tote filled with handy goods like a map, water and wet wipes. Plus, a drink of my choice to get me started. Time Out tip: if the drink is under $5, it’s free. If it costs more, like my iced matcha latte ($7.50), you’ll have to pay the remaining balance.
Before you embark on the trail, be sure to have a look at the little paper map in your tote bag. While it’s not the actual route, it's packed with handy prompts. Text ‘Help’ and you’ll see all commands, ‘Lost’ and you’ll get directions, ‘Stuck’ for hints, or go full panic mode with ‘SOS’ for immediate assistance. Think of it as the ‘Get Out of Jail Free’ card.
Where does the trail take you?
There’s no denying that Void Deck Cat kept me on my toes with riddles and puzzles. I took almost two hours to finish the trail, from SMU Connexion and National Museum of Singapore to Fort Canning Park and Clarke Quay. Without the photo stops and detours, thanks to a closed path, I reckon you can complete this in under 90 minutes.
Along the way, I uncovered corners of Fort Canning Park I’d somehow never stumbled upon, like the Spice Gallery and an archaeology site. Later, I found myself squinting at plaques in Clarke Quay, which turned out to be trickier than dodging tourists on a Friday night. And honestly? The journey is the real prize here. The game cleverly pulls you through heritage pockets and Insta-worthy spots, all while keeping your brain engaged with quirky tasks.
Where is the final stop?
Here’s where my luck ran out: the last checkpoint was closed for maintenance. Bit of a bummer since I couldn’t snap the big finale shot, but catching the sunset along the Singapore River softened the blow. If you’re planning to play, start around 4pm – you’ll dodge the midday heat and might score golden-hour views at the finish line.
What’s my verdict?
For $36.90, you get a self-guided adventure that you can start anytime and take as long as you’d like, as well as a goodie bag, and – most importantly – a fun new way to see the city. My only gripe? A free scoop of ice cream at the end of the trail would have been a nice finish. Still, if you’re looking for a fresh, interactive way to explore Singapore and get those steps in, this is a roll of the dice worth taking. Get your tickets here.
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