Olcott's sense of adventure prevailed again in 1904, leading him to Alaska. His journey ended notably when he drove a dog sled team to Nome, a trip of over 1,000 miles up the Yukon and Tanna Rivers in the height of winter. Settling in Fairbanks, Olcott found work as a gold dust teller, and later a bank branch manager. He managed to make a sizeable profit from gold prospecting, allowing him to move back to Oregon.