Southesk left Liverpool on 15 April 1859 on a Cunard paddle-wheeler called the Africa for North America. Eventually, he ended up in St. Paul, Minnesota, the jumping-off point for his expedition, and then continued on north to Fort Garry, the HBC's western headquarters in the Red River Colony. In June, Southesk, headed out west and over the next seven months, the expedition travelled more than 4,000 kilometres across the northern prairies to the Rocky Mountains. The plan was to head west out of Fort Garry into Rupert's Land, to hunt bears and bison. He arrived at Fort Edmonton on 1 August. At the fort he paused to buy horses, hired a Métis guide called Antoine Blandoine and built enough pack saddles to haul his outfit into the mountains west of the future site of Cadomin to pursue bighorn sheep. The journey, in early September, took the expedition up the Athabasca River to the McLeod River and finally, the Medicine Tent River, noting that he was now in country that, no European had ever seen, where bears and wild sheep were certain to be abundant. The expedition then crossed over Southesk Pass, to the Kootenay Plains of the North Saskatchewan River valley, in present-day Alberta. The expedition followed the Siffleur River, crossed over the Pipestone Pass, and followed the Pipestone River to the Bow River. After camping near Cascade Mountain, the Earl nearly crossed paths with another explorer, James Hector, at a time when there were very few Europeans in the Canadian Rockies.