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50 Incredible Oldest Towns In The US

oldest towns
Photo by Daniel M. Silva at Shutterstock

CONNECTICUT- WINDSOR
Established: 1633

Settlers from the Plymouth Colony built the first trading house in Windsor in 1633 on a patch of land they bought from Native Americans who were occupying the space. Today, the city uses its “oldest town” status to create a historical atmosphere, perfect for tourism.

DELAWARE- LEWES
Established in: 1631

This oldest town calls itself “The first town in the first state,” since Delaware was the first to ratify the Constitution. Lewes enjoys a particular sort of fascinating history. The charming town is full of historical traces and is a great place for a weekend getaway. There is plenty of nature to be found, as it’s located right where the Delaware Bay and the Atlantic Ocean meet.

FLORIDA- ST. AUGUSTINE
Established: 1565

Historians say St. Augustine is the oldest continuously occupied city in the US, established by the Spanish. It was established in September 1565 by Pedro Menéndez de Avilés, a Spanish soldier who chose the name because of the date he first saw it…it was the feast day of St. Augustine.

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28 thoughts on “50 Incredible Oldest Towns In The US”

  1. Hampton Virginia was established in 1610 and is the oldest, continuous English speaking settlement in the New World.

  2. Rendalynn Semans Simpson

    I sincerely want to thank you for description of Maryland. Maryland was settled as “The Free State,” for religious freedom. The democrat governor and failed president attemptee took away the free state slogan and made the official logo “The Old Line State.” Yes, it was the old line state, but it was for religious freedom before anything else.

  3. I lived in Astoria Oregon from 1957 to 1961. It was a thriving fishing town. The Navy had a base on the Columbia River. This was long before the bridge was built and ferries crossed the river to Washington. It was an interesting city. Small and friendly people.

    1. St. August, FL, is the oldest settlement of European origin in the US – established in 1655 and still going strong.

  4. I am a native Mississippian and have visited Natchez several times. Of all the things you COULD have said about Natchez (beautiful antebellum homes, Mississippi River town, casino, etc.), you chose to hang the “states most active slave-trading city” moniker around its neck. Is that the best you could do – perpetuate the city’s 200-years-ago history that no one is proud of today? Wouldn’t it have been better to describe it in a manner that would draw someone to the area? I thought that was the whole point of this article – to encourage people to visit the 50 oldest cities. That’s surely not likely to happen with that glowing (NOT) description of Natchez.

    1. Thank you for defending our wonderful Mississippi! I guarantee the racial divide is not nearly so wide here as in many other states. Mississippi is, for the most part, a deeply religious state, and we have learned from those terrible mistakes of the past.

  5. thank you so much my husband and i are retired and love to travel and we like to spend our $$$$$ in our country to keep our economy healthy so thanks again.

  6. I have been to Hawaii 4 times including Barbers Point and both Hickam Air Base & Pearl Harbor where I attended School 5th and 6th at Hickam and 7th at Pearl Harbor Intermediate. Lots of memories even at my age as you never forget the great times growing up.

  7. I Love Hawaii and still think it is the best place in the world as I have been there 4 different times with the first time growing up as I went to 5th and 6th grade at Hickam Air Base and 7th at Pearl Harbor Intermediate back in the 50’s.

  8. I lived in Providence,RI for many years. I’ve been to Connecticut a lot and also Massachusetts. I would definitely love to visit some more of the older states in my lifetime.

  9. Leonardo Francos

    I like 👍. I just retired and getting ready to travel and spend my money here in the US 1st many beautiful places to travel thank you.

  10. Been to Bath NC numerous times, as it lays across the Pamlico River where I reside in Chocowinity NC. A quaint town with no amenities that I’m aware of.

  11. Charles Michael Izzo

    Newark NJ might have been settled in 1666 but that was well after Burlington City NJ was settled in 1621.

  12. St. Augustine – oldest continuously occupied, but Pensacola was established in 1559 by Don Tristan de Luna and Spanish settlers and is America’s First (European) Settlement. The king and queen of Spain visited Pensacola in 2009 to commemorate the 450th anniversary of the 1559 Luna Expedition which established Pensacola. Magellan’s ship Elcano visited last year. Lots of heritage for both cities.

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