The route of The Dalles Military Road generally followed
Native American trails that were later used by white explorers such as
Peter Skene Ogden and
John Work on their travels through northeastern Oregon in the 1820s and early 1830s. In 1860, soldiers led by
Enoch Steen developed a military wagon road from
Fort Harney, near what later became Burns, to The Dalles. In 1862, more than 1,000 miners entered the region after gold was discovered on Canyon Creek, a tributary of the
John Day River. Many of them traveled from the
Willamette Valley and
Portland to The Dalles, where they followed established routes, including Steen's, to the John Day Valley west of what became Dayville and upstream to Canyon Creek. By 1864, the route was further improved, and mail, supplies, and passengers regularly traveled from The Dalles to Canyon City and the mines. To protect miners and other whites from the native peoples, who had not yet ceded this territory, the Federal government established military forts along the route. As early as the 1850s, the
United States Congress had been giving land to private companies to induce them to build railroads and wagon roads across the
West. Land grants for the five military wagon roads in the state totaled almost , whereas the total for all other states combined was about . Of these five, all but the Corvallis–Yaquina City road are considered to have been "almost total frauds" involving "local speculators" aided by "the connivance of state officials". Under the rules set by Congress, the land grants in Oregon passed to the state. When a private company completed part of the road, it could petition the Oregon governor to award the company 3 square-mile
sections of land for every of finished road. The private company was then free to sell or lease the land. In general, investors in the military roads chose routes through the most valuable land, such as potential farmland along rivers. A group of businessmen, mainly from The Dalles and doing business as The Dalles Military Road Company, chose the well-established route from The Dalles to Canyon City via the John Day River valley and from there to Fort Boise. The Oregon Legislature awarded the work to the company in late 1868. Governor
George L. Woods certified completion of the first in mid-1869 and completion of the entire route in early 1870. In part, the governor said, "I further certify that I have made a careful examination of said road since its completion, and that the same is built in all respects as required ... and that said road is accepted." Congress approved the land transfers in 1874, and in 1876 The Dalles Military Road Company sold the land to Edward Martin of
San Francisco for $125,000 (equivalent to $ today). Martin's Eastern Oregon Land Company acquired in sections within of either side of the road. ==Legal challenge==