Tuesday, November 18, 2025

Question: Which large city’s name was determined by a coin toss?

Answer: Portland, Oregon. Two of the city’s founders, Asa Lovejoy and Francis Pettygrove, both wanted to name it after their respective hometowns: Boston for Lovejoy, and Portland (for Portland, Maine) for Pettygrove. The two men agreed to a coin toss using an 1835 minted copper penny, now known as the Portland Penny, still safely housed in a museum. In any case, Pettygrove had heads. Lovejoy had tails. Pettygrove won two out of three tosses and the naming rights to the city. If the toss had gone the other way, the U.S. would have had two Bostons, one on either side of the continent.