According to Singapore Street Names, High Street is probably the oldest street in Singapore. Dating back to the founding of Singapore in 1819, it was laid by Lieutenant Henry Ralfe, a gunnery officer of the Bengal Artillery. During that time, Singapore was still largely forested. Ralfe and his soldiers were tasked to clear the land to create a meeting place for the signing of the preliminary treaty with the Temenggong of Johor.
The name High Street is appropriate considering it is on a higher ground than the river bank, thus it avoids any flooding. After High Street was laid, Hill Street and North Bridge Road were likewise laid. Along with Raffles Place, High Street was the choice retail centre for Singapore until Orchard Road overtook it. This is now a thing of the past, as High Street evolves away from its role as shopping street.