Once, the area around the Singapore River used to be the mainstay of Singapore’s Commerce. This is where Sir Thomas Stamford first landed in Singapore and set up Singapore as port. Many trading activities were held here at Boat Quay and Clarke Quay. It was the hub of Singapore's commerical activities during the 1800s. To this day, the buildings in area around Singapore River are preserved for heritage and tourism.

It is indeed a crucial place for us educate our younger generations about our past, right from the founding of Singapore by Sir Thomas Stamford Raffles. Furthermore, it allows different communities in Singapore to unite together as it serve as a place to remind us of our multi-racial past, present and hopefully future.

William Pickering was the first Protector of Chinese and at that time, he was the first European to be able to speak and read Chinese. He helped to curb the secret society activities and the stamped out of abuses of coolie trade. Pickering departed Singapore in 1888. Therefore, the street was named after him.

Kim Seng Road was named after Tan Kim Seng, a local philanthropist who lived in the 19th century. In 1857, Kim Seng donated $13,000 for improvements in the water supply of the town. A fountain at Esplanade Park was delicated to Tan Kim Seng for his contributions.

The street was so called as it is at the foot of Fort Canning Hill. The current the Ministry of Information, Communication and the Arts, is located on this street.

Once, the slopes of Fort Canning Hill used to extend as far as the old Parliament House. High Street was so called as it was built on higher ground.