Portland, OR City Guides

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But for the toss of a coin, you might be reading the Insiders’ Guide to Boston, Oregon. Early settlers Asa Lovejoy and William Overton brought their canoe ashore at a clearing in the woods along the Willamette River. Both men agreed that it looked like a promising site for a town. But Overton, a drifter from Tennessee, lacked the 25 cents he needed to file a land claim. So he struck a deal with Lovejoy: They would share the 640-acre site if Lovejoy would put up the money, and the two filed a claim in 1842. But soon, Overton tired of the pioneer’s life, and he sold his half of the claim to Francis Pettygrove. By 1845 the settlement in the clearing in the woods had grown enough so that the two owners knew they had to name their site. Pettygrove, a native of Maine, favored the name Portland, while Lovejoy, who came from Boston, wanted to name it after his fair city. The two men agreed to settle the matter by flipping a copper penny. Pettygrove won, and you can still see the “Portland Penny” on permanent display at the Oregon History Center.

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