7:00 PM – 7:15 PM (15 mins) – Checkpoint 1: Peranakan Museum and Armenian Street Begin the tour with a meet-and-greet and an introduction to the main themes of the experience. Learn about Peranakan culture—its unique blend of Chinese and Malay traditions—and the historical importance of the former Tao Nan School building. This section also introduces the role of oral histories in understanding the heritage of the area.

7:15 PM – 7:30 PM (15 mins) – Checkpoint 2: The Substation Enjoy a storytelling session outside this iconic arts venue while learning about its origins as a former power substation and its evolution into Singapore’s first independent contemporary arts centre. This segment highlights how arts and culture shape and express national identity.

7:30 PM – 7:45 PM (15 mins) – Checkpoint 3 and 4: Armenian Church and Freemasons’ Hall Take a guided walk along Armenian Street with stops at two significant historical landmarks. Learn about G.D. Coleman’s colonial architectural influence, the contributions of the Armenian community, and the role of the Freemasons in Singapore during the colonial period.

7:45 PM – 8:05 PM (20 mins) – Checkpoint 5 and 6: Fort Canning Green and Archaeological Dig Site Begin the ascent up Fort Canning Hill, exploring the history and significance of the Old Christian Cemetery. At the archaeological dig site, the focus shifts to 14th-century Temasek, highlighting discoveries that reveal the existence of a thriving pre-colonial port city.

8:05 PM – 8:25 PM (20 mins) – Checkpoint 7: Keramat Iskandar Shah Make a respectful visit to this sacred shrine while exploring the stories of Sang Nila Utama and Iskandar Shah. This segment delves into the Sejarah Melayu (Malay Annals) and the rise of the Kingdom of Singapura, offering key insights into Singapore’s pre-colonial Malay heritage.

8:25 PM – 8:45 PM (20 mins) – Checkpoint 8 and 9: Fort Canning Centre and Fort Gate Explore the summit of Fort Canning Hill while learning about its military past—from its days as a British Army barracks to the crucial role of the Battlebox during World War II and the events leading up to the surrender of Singapore.

8:45 PM – 9:00 PM (15 mins) – Checkpoint 10 and 11: Pancur Larangan and Tour Conclusion Descend Fort Canning Hill and conclude the tour with a final storytelling session at Pancur Larangan, reflecting on the hill’s rich history and the legends encountered throughout the journey.