[3] At its northern end near Martin Place, the street is lined by many of Sydney's most expensive boutiques and jewellery stores,[4] such as Chanel, Gucci, Cartier, Bvlgari, Dior, Dolce & Gabbana, Hermes, Prada, Van Cleef & Arpels, Ermenegildo Zegna, Omega and Mont Blanc.

[5][6] Castlereagh Street once contained the Australia Hotel, whose foundation stone was laid by Sir Henry Parkes, and the Theatre Royal.

It was an extremely busy service for passengers transferring from suburban trains, particularly prior to the opening of the City Circle underground railway line in 1926.

The line closed on 27 September 1957 with four tram services replaced with buses and three others diverted to operate via Elizabeth Street.

[7][8] The line made use of the sandstone viaduct onto the colonnade above Eddy Avenue at Central station, which since 1997 has formed part of the Inner West Light Rail.