McCubbin was born in Melbourne. McCubbin was taught at William Willmett's West Melbourne Common School and St Paul's School, Swanston Street. He worked several jobs while studying art at the National Gallery of Victoria's School of Design. There he met Tom Roberts and studied under Eugene von Guerard. He also studied at the Victorian Academy of the Arts. He showed some of his early paintings there in 1876, and again from 1879 to 1882. He sold his first painting there in 1880.