The next time you’re in town with time to kill, forget whiling it away in a cafe and try wandering through a cemetery instead.

A brand new heritage trail spanning the Orchard area has been unveiled, packed with history and lesser known stories of our city’s most famous shopping street. The 18th in the National Heritage Board’s (NHB) list of heritage trails, the Orchard Heritage Trail is a self-guided trail around 71 heritage sites spanning Dhoby Ghaut to Tanglin.

The cemetery in question actually no longer exists; the former Tai Shan Ting cemetery was exhumed in the 1950s by Ngee Ann Kongsi, to make way for what is now Ngee Ann City and Wisma Atria. While the association used the money to raise funds for its charities, the remains of the cemetery were reinterred to the Teochew Memorial Park at Yishun.

Meet the man who conducts heritage trails around neighborhoods in Singapore.

It’s part of the “Communities and Cemeteries” route, an hour-long trail exploring the places of worship, schools, homes, and cemeteries in Orchard. The route is one of three curated thematic routes for a more focused experience—“From Orchard to Garden” takes nature lovers on a two-hour walk through the green spaces that exist or used to exist there, while “Orchard Road’s Historical Gems” is a more general primer to the area’s historical landmarks and legacies, such as Singapore’s first department store C K Tang, and The Heeren.

Trail markers have also been put in place to help chart Orchard’s metamorphosis, from a community of nutmeg plantations to today’s retail and tourism hub. You can look forward to learning more about Singapore’s first skyscraper (The Cathay), Singapore’s first supermarket Cold Storage (housed in present-day The Centrepoint), the former Orchard Road Police Station (now ION Orchard), the former Glutton’s Square and more.

The Cathay. Photo credit: Urban Redevelopment Authority

Cuppage Terrace. Photo credit: Urban Redevelopment Authority

Jury’s still out on how a heritage trail in Orchard will make you feel—yay to our rich history and progress, but nay to the fact that so many historical places have been lost and turned into malls? (The word ‘former’ is starting to give us PTSD.) The exhuming of graves has been a topic of discussion for a while now, and we all know heritage and conservation continues to be a tricky conversation to navigate. NHB’s head is in the right place, but a trail like this is bound to generate even more buzz.

If you missed the art walk around Emerald Hill organized by OH! Open House earlier this year, this one might be worth checking out. You won’t get audacious artworks of Sir Stamford Raffles used as a kueh kapik roasting tray, but it’ll likely still be a fun primer to Orchard’s riveting history.