Pensacola, Florida

Pensacola was originally established by the Spanish in 1559, which places it squarely at the top of the list of oldest cities in the US (This fact is disputed by St. Augustine, which claims that because it has been permanently settled since 1561 it should hold the honor). Whichever way you look at it, Pensacola has around 450 years of history to share. You can learn a lot about the early years by following the Colonial Archaeological Trail, which winds through downtown Pensacola, visiting various ancient ruins and fortifications. You can also walk in the footsteps of the soldiers and settlers at Fort Pickens and visit Historic Pensacola Village. Younger visitors will enjoy the Pensacola Children’s Museum and the National Naval Aviation Museum. 25 of the Oldest Cities in the United States - Photo: Ulf/Fotolia

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