Hillside is one of several landscapes of the Goulburn River valley in central Victoria that Roberts painted in November 1927. He and his wife Lillie took three weeks holiday at Trawool; Arthur Streeton was also staying there.

Streeton’s efforts from this time were rewarded when he received the 1928 Wynne Prize for his Afternoon light, Goulburn Valley 1927. Roberts’ Hillside was painted at the same time and is of the same west valley view but is taken from a vantage point to the right of Streeton’s position and captures the morning light.