W. Harry Hembree was a ship builder and captain. His paternal grandfather was in the French Navy and traveled to America by private ship, selling his ship to the United States for 6,000 acres of land. In America, Hembree's grandfather owned eighty slaves, which were freed before the journey to Oregon. Hembree's grandfather, father and uncle traveled to Oregon from Missouri by wagon train, arriving in La Fayette, Oregon in 1843. The family became farmers and also built stores in La Fayette and McMinnville. Hembree's stepfather, Jason Kellogg, traveled to Oregon in 1849 from Maine. He worked as a fisherman in Maine, but came to Oregon and worked as a fur trapper. By the 1860s, the Kellogg family had built a boat and begun transporting freight along the Tualatin River. The family hauled freight with a barge along Lake Oswego, to the Willamette River, and to Portland. The Kellogg's cleared the rivers and built locks in the lake in order to run boats and barges along these waterways. They ran a successful company from 1875 to 1920, running a boat along the Cowlitz River. The Kelloggs maintained a variety of boats in the Portland area during the late nineteenth century and early twentieth century.

During the late 1800s, W. Harry Hembree went to high school at the Portland Academy. After high school he worked with his family on boats, before attending Willamette University for two years. Hembree traveled to Oakland, California, to work for the Mining Engineering School. Later, Hembree worked as a captain in Oregon delivering freight along the Willamette River. In his later years, Hembree became interested in pioneer wagon train journeys, and read accounts of journeys and attempted to retrace the route of a particular journey from Ft. Boise to Oregon.