Discover the history and charm of the oldest cities in the USA, from New Castle to St. Augustine. Learn about their founding dates, colonial influences, historical landmarks and cultural attractions. · St. Augustine wins the age contest by a comfortable margin, predating the next oldest American city by over 40 years. The Spanish established this settlement as a military outpost, and it has been continuously inhabited ever since, making it America’s oldest city by any measure. 1 day ago · From colonial outposts to vibrant cultural hubs, these 22 oldest cities offer a fascinating glimpse into America’s past and present. How many have you visited on your journey through history? America’s oldest cities hold a unique place in the nation’s history, with some dating back over 460 years. The oldest continuously inhabited city in the United States is St. Augustine, Florida, founded in 1565, making it a living reminder of early colonial history. · Founded by Spanish explorer Pedro Menéndez de Avilés, St. Augustine holds the distinction of being the oldest continuously inhabited European settlement in the United States. This charming coastal city predates Jamestown by more than four decades and continues to showcase its Spanish colonial heritage. · Discover the top 10 oldest cities in the U.S., including St. Augustine, Jamestown, and Santa Fe. Explore their founding years and historical significance.