The city whose name was famously decided by a coin toss is Portland, Oregon.

Quick Scoop: The Coin Toss City

Back in 1845, two New England pioneers were arguing over what to call a little settlement in the Pacific Northwest.

  • Asa Lovejoy wanted to name it after his hometown, Boston, Massachusetts.
  • Francis Pettygrove wanted to name it after his hometown, Portland, Maine.

They settled the dispute in the most low‑tech way possible: a best‑two‑out‑of‑three coin toss, using what’s now known as the Portland Penny , an 1835 copper U.S. cent. Pettygrove won the toss, so the town was named Portland instead of what might have been another “Boston” on the map.

Fun “What If?”

If Lovejoy had won, today’s largest city in Oregon would likely be called Boston, Oregon , and trivia fans would have one less legendary coin‑flip story to tell.

TL;DR: The answer to “what city’s name was decided by a coin toss” is Portland, Oregon , named after a coin flip between two founders who wanted Boston vs. Portland.

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