The Press was first published on May 25, 1861 from a small cottage in Montreal Street, making it the oldest surviving newspaper in the South Island. The first edition was a six page tabloid and was sold for sixpence. The paper continued as a weekly with the driving force behind the paper being James Edward Fitzgerald. On 13 June 1863, the first part of Samuel Butler's Erewhon appeared in the Press Newspaper in an article signed Cellarius and headed "Darwin among the Machines.
In 1905 The Press purchased a block of the current site for £4000. The Board then purchased the right of way (Press Lane) and what was going to be the original Theatre Royal site from the Theatre Royal Syndicate for £5000. The Gothic part of the building now still occupied by the company,was started being built in 1907 and the Press staff shifted into it in February 1909 from their Cashel Street premises.
In the 1930s, The Press began to seek solutions to the slow delivery times of the newspaper to the West Coast. Roads at the time were difficult, and the New Zealand Railways Department was unwilling to re-schedule any of its ordinary passenger trains to operate at the early morning times desired by The Press as patronage would have been uneconomic, and freight trains did not provide a desirable measure of swiftness. Accordingly, The Press was willing to subsidise the construction and operation of two small Leyland diesel railbuses to carry the newspapers by rail at a desirable time. These little railbuses began service on August 3, 1936 and left Christchurch at 2:20am, travelling down the Midland Line to reach Greymouth at 6:40am and then continue along the Ross Branch as far as Hokitika, arriving just before 8.00 am. This provided substantially quicker delivery of the newspaper than was previously possible. However, these railbuses were intended to only be a temporary measure and they were replaced by the much larger Vulcan railcars as soon as they arrived in New Zealand in the early 1940s.
Today, the newspaper is a well respected member of the four main daily newspapers, circulating over 90,000 papers per day through the South Island.
The Press won the Best New Zealand Newspaper award and also picked up Best Daily Newspaper with a circulation over 25,000 at the 2006 Qantas Media Awards, and won the same award again in 2007. It is the first time since 1991 that any New Zealand newspaper has achieved this feat. It also won several other awards including best-in-field awards for its "Zest" and "Drive" sections.