We begin our journey at the infamous Orchard Towers – a landmark that has seen its fair share of stories. From there, we trace the remarkable rise of Orchard Road, today Singapore’s most famous shopping street.

Like many parts of Singapore, Orchard Road began humbly. In the early days, the land was mainly agricultural, with gambier and nutmeg plantations scattered across the area. These ventures struggled, but the seeds of change were already planted.

By the turn of the century, Orchard Road began to transform, and by the 1950s it was well on its way to becoming the glamorous boulevard we know today – thanks in part to the colonial community and the Peranakans who brought colour and flair to its lifestyle.

Today, Orchard Road dazzles with world-class shopping malls, luxury hotels and glitzy nightlife. But beneath the surface lies a far richer story. While many tourist guides highlight its beauty, I will take you deeper – from Orchard’s fairy-tale beginnings to the turbulent decades of the 1960s and 70s, when it was marked by less glamorous chapters, including its drug-laden past.

And because most of us love a happy ending, we will close the walk with uplifting tales of Orchard Road’s renewal and its place in modern Singapore – a road that continues to reinvent itself while keeping echoes of the past.

This walk is not just about history – it’s about seeing Orchard Road differently. Along the way, we’ll stop to appreciate landmarks that are often overlooked or quietly omitted from the glossy brochures.

Our walk concludes near Dhoby Ghaut, at what was once the former car showrooms along Oldham Lane. Long before Orchard Road became the land of high fashion, this was where the wealthy came to buy their horses and carriages, later giving way to motor cars.

Meeting Point
We gather at Orchard Rendezvous Hotel, 1 Tanglin Road, at 9.00am sharp. Look out for me with my Tourist Guide badge.

Join us for a heritage walk that peels back the layers of Orchard Road – from plantations to glamour, from struggles to success. Discover the Orchard Road few talk about, but everyone should know.

For reservations, contact:
UNCLE CHRIS WALKING TOURS
Chris WK Ng
T: 65 91814298
E: [email protected]
W: www.unclechrisdrivingholidays.com

Note:
• We do the worldwide practice of tipping at the end of the tour.
• We also reserve the right to accept or reject habitual late cancellations and No Shows.
• Do not sign up for this tour if you are not sure of your schedule. Sign up only when you are sure of your schedule.