The first to be built in Singapore in 1819

High Street was the first street to be constructed in Singapore by the first town planner Lieutenant Henry Rafle, Gunnery Officer, Bengal Artilerry, East India Company. Rafle and his soldiers had to clear some part of the jungle near the shore to create a meeting place for the signing of the preliminary treaty with Temenggong Abdul Rahman in 1819.

In the same year Hill Street and North Bridge Road were laid out. The streets were simply named : Hill Street was at the foot of Government Hill, North Bridge Road because it was north of the Singapore River and later South Bridge Road because it was south of the River. When a new bridge was built the road was named New Bridge Road. 

High Street used to be the most import street in the city and was the main shopping centre before Orchard Road overtook it.