Dempsey Hill has long stood as one of Singapore’s most cherished lifestyle destinations, where the past and present coexist in perfect harmony. With its rich colonial history, lush greenery, and it’s wide selections of restaurants, it provides visitors with a unique blend of historical charm and contemporary appeal.
The recent introduction of a heritage audio tour further elevates the experience, offering an immersive way to uncover the captivating stories that have shaped this iconic location in Singapore.
The starting point of the audio tour, Dempsey Hill Fountain
For all history enthusiasts, the newly launched heritage audio tour, available for booking on Klook, is a must. The self-guided journey takes visitors on an immersive exploration through the lush greenery and historical architecture of the area, revealing fascinating stories from its past.
Photograph of Kerry Taylor, driver with the British Army in Tanglin from 1963 until 1965
Dempsey Hill’s history dates back to the mid-1800s, when it was originally known as “Mount Harriet.” By the 1860s, the area became the Tanglin Barracks, a pivotal military hub during Singapore’s colonial era. The tour takes visitors through the evolution of Dempsey Hill, from its humble beginnings as a plantation to its time as a bustling military enlistment center, and finally, to its transformation into the vibrant lifestyle hub it is today.
Main Entrance from Holland Road to Minden Road – Credit to Garry Bennet
Left Cookhouse now demolished, Centre Dining Hall block 11 and Right north end of Block 8 – Credit to Garry Bennet
One of the standout features of the audio tour is its flexibility. Visitors can pause the audio at any time, allowing for moments of reflection while soaking in the beautiful surroundings or enjoying a coffee at one of the charming cafes along the way. Priced at just $25 per person and lasting around 40 minutes, the tour offers a perfect balance of history and leisure.
After immersing in the history of Dempsey Hill, visitors can indulge in the diverse cafes and restaurants that define the area’s vibrant dining scene. Renowned for its gastronomic excellence, Dempsey Hill offers a rich array of flavors and experiences to satisfy every foodie’s palate.
Interior of Magarita’s with curated artworks and mural painted by Lasalle students
The Carajillo, a mexican cocktail made with espresso
A refreshing Ceviche with cured Halibut, Avocado Lime Puree, Hibiscus Tortilla Taco, Guava Shrimp, Sauteed Onions, and Corncake with honey-roasted peppers, pickled jalapenos, and queso.
Magarita’s in-house Teqila
Mole Pork Ribs, Mole Poblano, Apple Prune Salad, Ancho Chile
Magarita’s famous Magarita!
One of the standout spots at Dempsey Hill is Margaritas, one of the first few restaurants to open in the area. The restaurant offers an authentic Mexican experience, famous for their Magaritas. If in need of a pick me up, try the Carajillo, a unique Mexican drink made with espresso, Licor 43, and a shot of tequila. What sets Margaritas apart is their in-house tequila, crafted in Mexico, giving it an authentic and unique touch. Additionally, Margaritas takes pride in their homemade ice cream, crafted in-house to complement their vibrant dishes, creating a complete culinary experience that showcases the true flavors of Mexico.
Chang Korean Charcoal BBQ
Whether visitors are in the mood for an indulgent brunch, a leisurely lunch, or a sophisticated dinner, Dempsey Hill’s restaurants serve a range of dishes for all the foodies. The atmosphere at these establishments is casual yet elegant, making them the ideal spot to relax and enjoy a meal with friends and family surrounded by the natural greenery.
What makes Dempsey Hill truly special is how it seamlessly blends its rich colonial history with the modern-day attractions it now offers. The heritage audio tour and the updated restaurant menus are just two examples of how Dempsey Hill continues to elevate the visitor experience in 2025. This unique combination of history, culture, and gastronomy makes it the perfect destination for those looking to explore Singapore’s past while enjoying its vibrant contemporary scene.
Siri House
Da Paolo
Dempsey Hill is a must-visit destination for anyone looking to experience the charm of Singapore’s past while indulging in a variety of delicious cuisines. The combination of the heritage audio tour and the variety of dining options make for a fun experience suitable for those that want to learn more about the history of such a iconic Singapore landmark. Whether you’re a history enthusiast, a food lover, or simply seeking a relaxing day out with friends and family, Dempsey Hill offers something for everyone.
Don’t miss out on the opportunity to explore this iconic locale in a new way—book the audio tour on Klook and immerse yourself in the stories that have shaped Dempsey Hill.
The Dempsey Hill Immersive Audio Tour is available for booking via Klook. Don’t miss the chance to uncover the hidden stories of this charming location. For more information and to book your tickets, visit Klook’s Dempsey Hill Audio Tour page.
