The Oldest Cities in the United States

There are over 108,000 cities in the United States and its territory. However, with the United States being founded in the late 1700s and the latest territories being added in 1947, the cities found here vary in age. You’ll find the oldest cities in the U.S. are widely distributed around the country, and they have a rich history.  

Ready to learn more? Here are the four oldest cities in the U.S. — plus six honorary mentions!

1. St. Augustine, Florida

Pedro Menéndez de Avilés, a Spanish admiral and the first governor of Florida, founded St. Augustine on September 8, 1565. He named the land San Agustín because his ship sighted land on the feast day of St. Augustine. This makes St. Augustine the oldest continuously inhabited, European-established settlement in the United States.

The city has had a fluctuating history, changing hands among European countries. It served as the capital of Spanish Florida until the 1700s. In 1763, the British formed a colony and made St. Augustine the capital of British Florida. Just twenty years later, in 1783, Spain regained control of Florida. In 1819, Florida joined the newly formed United States.

Once a U.S. territory, Florida initially designated St. Augustine as its capital. However, the city relinquished this title in 1824 when Tallahassee became the new capital.

With nearly five hundred years of history, St. Augustine is home to hundreds of sites and monuments that showcase its rich past. Notable figures like Zora Neale Hurston and Ray Charles hail from this ancient city.

Best Time to Visit

While some may say that anytime is the best time to visit, as the weather is generally great and there are festivals year-round, the ideal time is in the spring and fall. The temperature is relatively comfortable, and there aren’t as many crowds. There are many activities, like trolley tours, to see and do, like fishing.

2. Jamestown, Virginia

Although St. Augustine may be the oldest city in the U.S. overall, Jamestown is the oldest English settlement in the country! The very first English settlement in all of North America, Jamestown, was founded on May 14, 1607.

Like many other countries first founded in the early days of the United States, the venture to Jamestown was a private one. This means that it was conducted through a business rather than as a government affair. However, King Jams, I did contribute some charters to aid in the journey’s success into the New World.

The fleet carrying the founders of this old city arrived in the Chesapeake Bay on April 26, 1607, after having departed from England in December of the year prior.

Best Time to Visit

Based on the weather alone, the best time to visit Jamestown, Virginia, is in the spring or early fall. The weather can range from 62 to 81 degrees in spring, and the fall brings temperatures from 81 to 62 degrees. While there is a lot to see and do year-round, the blooming gardens in spring and the fall foliage in autumn are something not to be missed.

3. Pensacola, Florida

The city of Pensacola, Florida, holds the title of the oldest European settlement in the U.S. despite an early setback. Spanish explorer Tristan de Luna sailed into what we now call Pensacola Bay in August 1559, under orders from Luis de Velasco, Spain’s viceroy of Mexico, to establish a settlement there.

De Luna arrived with a fleet of 11 ships and 1,500 settlers, including Mexican Indians and African slaves — many of whom were craftsmen — six years before Adm. Pedro Menendez de Aviles landed at what is now St. Augustine. Activity bustled in the settlement, originally called Pensacola after the local Muskogean tribe’s term “Panzacola,” which means “hair people.” However, a powerful hurricane struck on September 19, 1559, sinking all but three of Luna’s ships.

One ship sailed to Mexico to seek help, while the settlers stayed on for over a year, their supplies and numbers dwindling. Eventually, only a military outpost survived until Spain established another garrison in 1698, which then grew into a colonial town.

Today, Pensacola boasts a historic district of 40 blocks of beautiful Spanish and French-style buildings, shaded by ancient live oaks. The city is home to one of the largest naval bases in the U.S., and home to the famed Navy “Blue Angels,” who treat the beachgoers to airshows and practice runs from March through November. The city on Pensacola Bay is just minutes across a bridge to the beautiful Pensacola Beaches – with pristine white sand and sea oats among the dunes – one of the prettiest beaches in the country.

Best Time to Visit

If you want to enjoy the beautiful beaches of Pensacola as well as the historic city — the best time to visit is late spring to early summer — April through June. If you like the beach but aren’t going to swim and tan — fall is a great time for a beach vacation. The weather is pleasant, and the crowds have thinned out. Fall is also a good time for fishing!

4. Santa Fe, New Mexico

When you think of the oldest cities in the U.S., your mind probably goes to cities along the eastern coast of the country. After all, many of the people who arrived to colonize this land came from Europe, so the East Coast would be their first stop!

However, the third oldest city is actually found much further west: in Santa Fe, to be exact. Santa Fe was founded in 1610 by Governor Don Pedro de Peralta. This makes it just a few years older than the first English settlement in Virginia. During this time, it was named Villa Real de la Santa Fé de San Francisco de Asis. That translates in English to the Royal City of the Holy Faith of St. Francis of Assisi. Talk about a mouthful! Now, the city is known simply as Santa Fé, or Holy Faith.

Best Time To Visit

As Santa Fé is located in the west, it would seem that any time is the best to visit. Temperatures do have a wide range in this area, but with averages in the high 20s to the high 70s, the best time to visit is September through November, when the greatest amount of festivals take place.

6 Other Interesting Old Cities in the United States

Although these cities may not be the oldest in the entirety of the United States, they still have their roots dating back hundreds of years ago. However, they’re also exceptional due to other historical facts that contributed to the United States becoming the country it is today. Here are six other interesting cities that also just so happen to be some of the oldest in the country.

1. Annapolis, Maryland

Annapolis is the capital city of Maryland. In 1649, settlers established a community in this area and called it “Providence.” It wasn’t until 1694 that the settlement adopted its current name, Annapolis, in honor of the Princess Anne of Denmark and Norway.

Situated at the mouth of the Severn River on the Chesapeake Bay, Annapolis boasts a rich history as a port town. Puritan exiles from southern colonies like Virginia first settled here, taking advantage of the harbor’s safety and access to seas for transport and trade. Over time, fishing, oyster packing, boat building, and sailmaking emerged as the town’s main industries and occupations.

One remarkable fact about Annapolis, Maryland, is its stint as the temporary capital of the entire United States following the signing of the Treaty of Paris in 1783. In that same year, George Washington resigned from the Continental Army in Annapolis.

While people initially planned to draft and sign the original Constitution in Annapolis in September 1786, the meeting that occurred here instead laid the groundwork for the Philadelphia convention, where delegates eventually created the Constitution.

2. Boston, Massachusetts

Not only is Boston one of the largest cities in the country, but it is also one of the oldest!

Founded in 1630 on the Shawmut Peninsula, Boston took its original name from the Algonquian word “Mashauwomuk.” While the meaning of this word remains largely unknown, records show its use to describe the area of future Boston around the time of the city’s colonial inception. Puritans, who derived their name from an English town they left, established Boston.

Serving as one of the oldest cities in the United States, Boston played a significant role in the American Revolutionary War. The city hosted numerous key historical events, such as the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill, and the Siege of Boston.

Boston also claims many historical “firsts” in the emerging United States. The city established the first public park in 1634 and launched the first subway system in 1897, among other technological and socio-economic advancements.

However, this is only Boston’s history as one of the oldest cities in the United States. When you look at the Native Nations that inhabited the land first, you’ll find thousands of years of history embedded in the Shawmut Peninsula. In fact, one of the oldest fishing weirs in the United States, the Boylston Street Fishweir, can be found here. 

3. Charleston, South Carolina

Not only is Charleston one of the oldest cities in the U.S., but it is also the largest city in South Carolina, where it was once the capital. You can trace this old city’s roots back to 1670. When it was first founded, it was known as Charles Town. This was in honor of King Charles II, the King of England, Scotland, and Ireland at the time.

At first, Charleston was located in an entirely different area. Its original location could be found at Albemarle Point. This is on the west bank of the Ashley River, where today you can find Charles Towne Landing. Charleston remained here for around ten years. In 1680, it was moved to its modern-day location. 

It was a good thing it moved, too! Within ten years, Charleston became the fifth-largest city in the United States at the time. 

While it only took the city around a decade to move from Albemarle Point to its current location, it took much longer for its modern-day name to come about. Charles Town didn’t turn into Charleston until around 1783 when it became incorporated into an official city. Although it continued to be a successful and flourishing city, the title of capital was relocated to Columbia in 1788.

Prior to all this, however, in the late 1600s, Charleston was a hot spot for pirates. Because the city remained unincorporated for so long, it was viewed as weak, which allowed for increased crime. This, paired with the location on the water, made it an easy target for raids. 

4. Detroit, Michigan

The city of Detroit is known for many things. First, it’s the largest city in Michigan. It also happens to be the largest U.S. city on the United States – Canada border. As of 2020, it had a population of 639,111 — making it the 27th-most populous city. Out of tens of thousands of cities across the entirety of the United States, these are some pretty impressive ranks!

Detroit is also one of the oldest cities in the United States, adding another title to its claim to fame. It hasn’t always been a city, however. Before the Detroit we know was Detroit, it was the Fort Pontchartrain du Détroit. This fort was founded in 1701 by Antoine de la Mothe Cadillac and Alphonse de Tonty. 

At this time, however, Detroit wasn’t considered a part of the United States or the British Colonies. It didn’t become a part of the colonies until the French and Indian War. During this, it was surrendered to the British in 1760. 

During the Industrial Revolution, Detroit experienced a major population boom as more people migrated from rural farms into cities for manufacturing jobs. In 1920, Detroit was the fourth largest city in all of the United States. The only cities larger at this time were New York City, Chicago, and Philadelphia. Much of this is thanks to the auto manufacturing industry that arose after the invention of cars. Thanks to its position on the Detroit River, it also became a major port, allowing businesses to continue to grow in the city. 

Today, the population has begun to decrease. It also became the largest city to file for bankruptcy in 2013, although it has since recovered. 

5. Honolulu, Hawaii

Honolulu is the capital city, as well as the largest city on the islands of Hawaii. It is found along the southeast coast of the island of Oʻahu, making it both the westernmost and southernmost city in all of the United States. 

This city has a rich history that goes even beyond the United States. It first became the capital of the islands during the time of the independent Hawaiian Kingdom in 1845. Honolulu continued to be the capital of the Hawaiian Kingdom until Queen Liliʻuokalani was overthrown in 1893. However, once the United States gained the territory, Honolulu remained the capital city of the new state, which was annexed into the country in 1898. 

Honolulu was the site of the Japanese attack on Pearl Harbor in 1941.

6. Jersey City, New Jersey

Before Jersey City was the city we know today, the land belonged to the Lenape. We can first trace European interactions in the area to 1609, when English explorer Henry Hudson landed in the area. Seeking a new route to reach East Asia, Hudson had anchored his ship, the Halve Maen, along different points in the North River. 

It was only a few years later, in 1621, that the Dutch West India Company set out to manage this territory. In the summer of 1623, the area became known as New Netherland. Then, in 1630, Michael Reyniersz Pauw received a land grant with the stipulation of creating a settlement. He purchased the land from the Lenape and did just that, creating a settlement that is now Hoboken and Jersey City.

Due to mismanagement, the settlement and its relationship with the Lenape deteriorated throughout the years. 

Then, in 1804, Alexander Hamilton established the Associates of the Jersey Company. The Treaty of 1834 gave New Jersey the rights to Jersey City, created by Hamilton’s Associates, and the Jersey Company applied to have the City of Jersey incorporated. It received its modern-day name on February 22, 1838, and it became part of Hudson County exactly two years later. 

In the 19th century, Jersey City was an escape haven for slaves who traveled through the Underground Railroad. It later became one of the first stops for immigrants as well. As they made their way inland from Ellis Islands, tens of thousands of people passed through Jersey City’s train stations. 

The photo featured at the top of this post is © iStock.com/felixmizioznikov