First and Oldest City Challenge


The first and oldest city challenge, takes you through the many icons and monuments of modern-day Singapore, all unique in their own way! We’ll show you how they’ve helped transform Singapore into the country we know today, and their relation to the five pillars of Total Defence- psychological defence, Social Defence, Civil Defence, and Military Defence. Together these approaches allow Singapore to tackle threats and are an integral aspect of Singapore’s prosperity and success as a nation today. As you embark on this trail, you’ll see their relevance in the everyday lives of Singaporeans and learn how you too can play your part.

  • Learn all about the rich heritage of some of Singapore’s oldest buildings.
  • Step into the premises of Singapore’s first church.
  • Explore museums galore along Armenian Street.
  • Istana
  • MacDonald House
  • National Museum of Singapore
  • Maghain Aboth Synagogue
  • Cathedral of the Good Shepherd
  • Tan Kim Seng Fountain
  • St. Andrew’s Cathedral
  • Armenian Church
  • Peranakan Museum (CLOSED)
  • Singapore Philatelic Museum
  • Central Fire Station
  • Raffles Residence at Fort Canning Hill
  • Masjid Omar Kampong Melaka
  • Former Thong Chai Medical Institution
  • Hong Lim Park

Recommended Start Time:

Monday to Sunday, 9:00am
Some places close by 5:00pm

Estimated walking distance

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