Portland Oregon (OR) started as a spot known as "The Clearing" which was on the Willamette about half-way between Oregon City and Fort Vancouver. In 1843, William Overton saw great commercial potential for this land; his only problem was that he lacked the quarter needed to file a land claim. So, he struck a bargain with his partner Asa Lovejoy: for 25 cents, Overton would share his claim to the 640 acre site.

Bored with clearing trees and building roads, Overton sold his half of the claim to Francis W. Pettygrove. When it came time to name their new town, Pettygrove and Lovejoy each wanted to name it after his home town. They settled the argument with a coin toss. Pettygrove won, and named it after Portland, Maine; had Lovejoy won, he intended to name it after Boston, Massachusetts.

In its early years, Portland existed in the shadow of Oregon City, the territorial capital twelve miles upstream on the falls of the Willamette. However, Portland was located at the Willamette's head of navigation, the furthest point inland one could reliably reach by ship. This gave it a key advantage over its older peer. It also triumphed over early rivals like Milwaukie. By 1850 Portland had approximately 800 inhabitants, a steam sawmill, a log cabin hotel, and a newspaper, called the Weekly Oregonian.

Portland was the major port in the Pacific Northwest for much of the 19th century, until the 1890s when direct railroad access between the deep water harbor in Seattle and points east by way of Stampede Pass were built. Goods could then be transported from the northwest coast to inland cities without needing to navigate the dangerous bar at the mouth of the Columbia.