Portland Oregon was chosen by a coin flip, otherwise, it would have been Boston Oregon.

In 1843, Tennessee drifter William Overton and his friend, Boston lawyer Asa Lovejoy were floating down the Willamette River in a canoe when they came upon the beauty of the place we now call Portland. They beached their canoe and they marveled at the beautiful mountains and the rich potential of the many trees they saw.

Overton didn’t have the quarter (25 cents) that was required to file a land claim, so he sold half of his 640-acre share to Lovejoy for 25 cents. They began to clear the many trees, build roads and build the first buildings. In June 1844, a destructive flood on the Willamette discouraged Overton, and he sold his half-interest in the claim to Francis W. Pettygrove for $50.

Portland got its name when Asa Lovejoy and Francis Pettygrove flipped a coin in 1845. Lovejoy was from Massachusetts and he wanted to name the new settlement Boston. Pettygrove was from Maine and wanted to name the new town Portland. Pettygrove won the coin toss two out of three times and the rest as they say is history.

More Info: en.wikipedia.org