Ann Siang Road connects Ann Siang Hill to Kadayanallur Street.
Before Chia bought the area, the hill was known as Gemmill's Hill after John Gemmill, a merchant and former auctioneer, and before that Scott's Hill, after its original owner Charles Scott, who cultivated nutmegs and cloves in the area.
The foot of the area between Ann Siang Hill and Mount Erskine, where South Bridge Road meets Neil Road and Tanjong Pagar Road (the site of the Metropole Theatre, now the Fairfield Methodist Church), was one of the earliest Cantonese Chinese burial grounds. The graveyard was in use up to 1867, exhumed in 1907 and part of the area, together with Mount Wallich, used for the Telok Ayer reclamation project.
The Chinese used to call this area qing shan ting. The early Chinese immigrants visited Ann Siang Hill when they wanted to send money home to their families in China as it was the traditional site of remittance houses. Letter writers and calligraphers also had their businesses at the five-foot way of the shophouses to help the illiterate immigrants write letters home.
Most of the houses in Ann Siang Hill and along Ann Siang Road were built between 1903 and 1941. Ann Siang Road, which has elegantly restored shophouses today, was once the traditional home of clan associations and exclusive social clubs.