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Although first sighted by Captain Watkin Tench of the Royal Marines on an expedition to explore the land west of Parramatta in 1789, the suburb of Penrith only sprung up after the completion of the Western Road which ran from Sydney out west towards the Blue Mountains. It is one of only a handful of towns which were not surveyed for use as a settlement but established slowly and organically due to its proximity to the Western Road and the Nepean River.

The population of Penrith began to flourish after the completion of St Stephens Church in 1838. This grand Gothic-style church seemed at odds with the sparsely populated farmland around it and seemingly invited a town to form around it. However, it was the extension of the railway line from Parramatta to Penrith in 1863 that gave the town its first significant growth by making the town easily accessible, providing employment as the line was extended across the Blue Mountains beyond it and providing the impetus for splitting the existing large land grants into smaller allotments to cater for the influx of residents.

The early 1900s proved a difficult time in the economic history of Penrith. With the railway expansion complete and crops and livestock farms proving far more successful over the ranges, Penrith's surrounding farms turned their hands to smaller produce farms such as market gardens and orchards as the city was promoted as a holiday spot for the city dwellers of Sydney. The post war urbanisation of Penrith which stemmed from the use of the area for a munitions factory during World War II would be the making of the town as Penrith was transformed from something of a farming suburb to a residential suburb.

The Penrith Planning Scheme of 1960 spelled the beginning of significant change with traditional farmland being transformed into industrial and residential space including a substantial amount of public housing throughout the 1960s and 70s. With Sydney's population explosion, the western suburbs have become popular for young families and the ample education and medical facilities in Penrith continue to make it a popular outer suburb.