Roberts painted 'An autumn morning, Milson's Point' during a visit to Sydney in early 1888. The painting depicts the northern shores of the harbour that were only accessible by ferry at this time. A contemporary reviewer attributed the murky colour of the air to the pollution as a result of burning coal. Later, Roberts himself lived and painted in this area whilst staying in Mosman at Curlew Camp, Sirius Cove, during the early 1890s.
Whilst in Sydney, Roberts met Charles Conder and the two became friends, painting together at Coogee beach. 'Holiday sketch at Coogee', by Roberts, is a celebration of the white sand and blue water of this popular promenade and bathing site, especially the intensity of Sydney sunlight. Roberts' time in Sydney proved extremely influential on the young artist, and Conder followed him to Melbourne later that year to join the group of artist friends at Heidelberg.