Possibly one of the best sites to learn more about the history of the Sydney area is the Dictionary of Sydney. To quote just a small excerpt..
Castle Hill Rebellion and the Battle of Vinegar Hill
In 1804 there was an uprising of 200 convicts, known as the Castle Hill Rebellion. They were mostly Irish and they planned to escape from the colony in boats, which they hoped were moored in Sydney harbour. The rebellion culminated in the Battle of Vinegar Hill, where the convicts were defeated.
Settlers grew wheat and raised sheep until more suitable lands were opened up to the west of the Blue Mountains. Citrus growing then took over and the Castle Hill area became renowned for its fine orchards.
by Joan Rowland 2008
You can also find more in Wikipedia
The following clips are from the first edition courtesy of the Catholic Press. Links to the rest of the articles are at the end of this post. Interesting times in the early days of colonisation. To enlarge the pages, just click on them or go to the underlined link to read the original.
Catholic Press (Sydney, NSW : 1895 - 1942), Thursday 28 April 1927, page 18 http://nla.gov.au/nla.news-article107972123
Further articles:
The Castle Hill Rebellion: Irish Exiles' Gesture of Despair 5 May 1927
Castle Hill Rebellion: Irish Exiles' Gesture of Despair 12 May 1927
The Castle Hill Rebellion: Irish Exiles' Gesture of Despair IV. 19 May 1927
The Castle Hill Rebellion: Irish Exiles' Gesture of Despair IV. The Castle Hill Rebellion. 26 May 1927
The Castle Hill Rebellion: Irish Exiles' Gesture of Despair V The Governor's Enemies. 2 Jun 1927