The Oldest Cities in the US – Most Historic Sites to Visit

The United States has an amazing and diverse history. Visiting the oldest cities in the US is a great experience to truly understand the culture and the people of this nation.

The arrival of Christopher Columbus in 1492 started the European colonization of the Americas. By the 1770s, thirteen British colonies contained 2.5 million people along the Atlantic coast. The United States was “formed” on July 4, 1776, but the oldest cities in the US were established long before.

Although most occupied lands that had been settled by Native Americans, most of the cities were founded by European explorers. The oldest cities in the US will reveal the secrets and history of this country to those who visit them.

Oldest Cities in the US – Saint Augustine, Florida

Founded: 1565
History of St. Augustine: St. Augustine, Florida is the oldest continuously occupied city in the United States. The Spanish explorer, Juan Ponce de Leon arrived to Saint Augustine in 1565 and proclaimed it a territory for Spain. St. Augustine remained the territorial capital until 1824 including the capital of Spanish Florida and British East Florida.

Where to Go in St. Augustine

St. Augustine’s distinct historical character has made the city a popular travel destination. When you go, take some time to appreciate well-preserved Spanish-style buildings and 18th- and 19th-century architecture. St. Augustine is a great city for walking. It has several oceanfront parks and a great climate which that allows for a full-year tourist season.

The heart of the city is its Historic District, that’s where you will find a majority of the city’s restaurants, shopping, hotels, and attractions. To learn more about the history of St. Augustine you should visit Fort Mose State Park, which is on the site of an 18th century fort. Also check out the St. Augustine Lighthouse, which was built in 1874 and provides a great view of the area. One of the best hotels to stay in is the Casa Monica Hotel. It is a Spanish-inspired hotel with great suites and a rooftop pool.

Traveler’s Tip: You should visit St. Augustine during December or January, to attend the famous St. Augustine Nights of Lights holiday. National Geographic selected the Nights of Lights twice as one of the ten best holiday lighting displays in the world.

Oldest Cities in the US – Jamestown, Virginia

Founded: 1607
History of Jamestown: The Jamestown settlement in the Colony of Virginia was the first permanent English settlement in the Americas and this town has an incredible historic significance.

When Jamestown was established, the colony faced troubled times. Within days of landing, the Powhatan Indians attacked the colonists. Disease, famine, and sporadic attacks from the neighboring Powhatan Indians took a tremendous toll on the early population of Jamestown. However, there were also times when trade with the Powhatan revived the colony with food in exchange for glass beads, copper, and iron tools.

Captain John Smith trained the first settlers to farm, which saved the colony from early devastation. It is also the same captain who was captured by the Pocahontas’ tribe. They eventually released him without harm. He later said that the chief’s daughter Pocahontas “threw herself across his body” to protect him. Smith said that “at the minute of my execution, she hazarded the beating out of her own brains to save mine; and not only that, but so prevailed with her father, that I was safely conducted to Jamestown”.

Where to Go in Jamestown

Jamestown is home to wonderful heritage sites related to the original fort and town: Historic Jamestowne and the Jamestown Settlement. Nearby, the Jamestown-Scotland Ferry service provides a link across the navigable portion of the James River for vehicles and affords passengers a view of Jamestown Island from the river. You should also visit the 1907 Memorial Church and the Archaearium, a museum that houses some of the most striking finds about the settlement.

Traveler’s Tip: In 2019, Jamestown will be commemorating the 400th anniversary of the First Assembly. The best time to visit Jamestown is in the Spring, there are usually a lot of events and festivals at the time and the weather is perfect!

Oldest Cities in the US – Santa Fe, New Mexico

Founded: 1607
History of Santa Fe: Santa Fe, New Mexico was occupied by indigenous peoples before Spanish arrived. Santa Fe is the second oldest city founded by European colonists in the United States. Santa Fe was the capital of the “Kingdom of New Mexico,” claimed for Spain by Coronado in 1540. In 1912, New Mexico was admitted as a state of the United States of America’s, with Santa Fe as its capital.

Where to Go in Santa Fe

Enjoy walking around the beautiful historic downtown in Santa Fe, especially on and around the Plaza. When in Santa Fe, visit the Palace of the Governors ($12 for non-residents), the original seat of New Mexico’s territorial government since the Spanish colonization.

Other places worth visiting: Museum Hill, the major art museum of the city and the Santa Fe International Folk Art Market, which takes place annually during the second full weekend of July. The Canyon Road arts area with its galleries is also a major attraction as well as the San Miguel Chapel which is the oldest church in the United States.

Traveler’s Tip: One of the best times to visit Santa Fe is the second week of September when the aspens in the Sangre de Cristo Mountains turn yellow and the skies are clear. This is also the time of the annual Fiestas de Santa Fe. It celebrates the “reconquering” of Santa Fe by Don Diego de Vargas. A highlight of the festival is the burning Zozobra (“Old Man Gloom”), a 50-foot structure.

Oldest Cities in the US – Plymouth, Massachusetts

Founded: 1620
History of Plymouth: Plymouth is on of the oldest cities in the US and it is well known in the United States for its historical value. The events surrounding the history of Plymouth have become part of the of the United States spirit. Most everyone heard about the Plymouth Rock, the Pilgrims, and the First Thanksgiving. The colony was settled by a group of religious dissenters commonly referred to as the Pilgrims. The explorer John Smith called the area Plymouth as the Mayflower had set sail from the port of Plymouth in England.

More than half the settlers died during the first winter, as victims of an epidemic disease. Soon, the Pilgrims met a Native American man named Squanto, who became a member of the colony. Squanto taught them how to plant corn as well as showed places to fish and hunt beaver. Agriculture, fishing and trading made the colony self-sufficient five years after its founding. Squanto was a mediator between Plymouth’s leaders and Native Americans. In the fall of 1621, the Pilgrims famously shared a harvest feast with the Pokanokets; the event that is now considered the beginning for the Thanksgiving holiday.

Where to Go in Plymouth

Plymouth has several historic lighthouses, including the Bird Island Lighthouse and Duxbury Pier Light. Don’t forget to visit famous Plymouth Rock and the Plantation.

Traveler’s Tip: The town is a popular tourist destination during the Thanksgiving holiday. This year’s Thanksgiving celebration will include special events. This is a part of the Celebration Series leading up to the anniversary of Plymouth in 2020.

Oldest Cities in the US – New York City, New York

Founded: 1609

History of NYC: The known history of New York City began with the Italian explorer Giovanni da Verrazzano in 1524. The Dutch were the first settlers of the area in 1609. The city served as the capital and hosted the inauguration of George Washington as the first President of the US. It was also the location for the drafting of the United States Bill of Rights. Here you will also find the first Supreme Court of the United States. In the mid-18th century, waves of new immigrants arrived from Europe through the Ellis Island, which dramatically changed the the city and its history. New York City holds an important cultural significance and everyone coming to the United States should visit this amazing city.

Where to Go in New York City

NYC is one of the main destinations on the United States bucket list! Learn more about the history of this remarkable city with a stroll along the Brooklyn Bridge, exploring the Central Park and the Empire State Building. Going to NYC will be the right place for anyone: there are so many options and activities from taking a photo at the famous Times Square to strolling in the Lower Manhattan to take a ferry to the Statue of Liberty or attending a Broadway Show. When you are in NYC, spend at least half a day shopping in some of the most famous shopping streets in the United States!

Traveler’s Tip: I found Groupon very useful when visiting NYC, it has a lot of worthy restaurant deals and coupons. Deals rotate, but last time we went, we enjoyed a good deal on Korean BBQ.  

Oldest Cities in the US – New Orleans, Louisiana

Founded: 1718

History of New Orleans: Even though New Orleans is closely associated with France, most of the famous architecture you will see in this city is Spanish. New Orleans was founded in 1718 by the French Mississippi Company. It was surrendered to Spain in 1763. The buildings from the French Quarter were built during the Spanish occupation. By 1801 the city found itself back in French hands, but Napoleon soon sold it to the United States in 1803 as part of the Louisiana Purchase.

Where to Go in New Orleans

You cannot visit New Orleans without going to the French Quarter. The neighborhood, also known as Vieux Carré, is the heart and soul of the city. The French Quarter has held on to its French heritage, so the street names are still in French. Wander the narrow cobblestone streets to find Jackson Square and the Faulkner House. Visit the historic French Quarter, Saint Louis No. 1 Cemetery, and the Bocage Plantation to learn more about the history of this one of the oldest cities in the US.

Traveler’s Tip: The best time to visit New Orleans is during the Carnival season and especially during the Mardi Gras Festival. But don’t worry if you go at other time, there’s always a party in NOLA, from poky jazz bars to smoldering blues clubs.

Oldest Cities in the US – San Antonio, Texas

Founded: 1717

History of San Antonio: Capturing the spirit and pride of Texas, San Antonio is a great place to learn more about the history and the culture of the region. From its Native American occupation, discovery by Spanish explorers, and the Battle of the Alamo, this city is an perfect location for exploring. The city is most known for the historic Alamo, the site of ‘crossroads’ in Texan history. Visiting the Alamo is one of the top experiences you need to have while in the United States. Here, important historical events took place, from the first Spanish colonization and the independence of Mexico to the place where the Confederacy stood its ground. 

Where to Go in San Antonio

No visit to San Antonio is complete without a tour of the Alamo, the most important battle site for the Republic of Texas. Visit Alamo to understand early Texas history and battle for Texas independence as well as Spanish architecture and artifacts. After you are done there, check out the Riverwalk and eat at one of the many restaurants.Then stroll on the San Antonio Riverwalk,which runs beside the scenic San Antonio River, an important lifeline to the city up to the present.

Traveler’s Tip: The San Antonio Museum of Art has one of the best collections of ancient Egyptian, Greek, Roman and Near Eastern art in the southern United States. Located on the River Walk, the museum hosts over 500 guided tours each year. This could be appealing to adults looking to learn more about art as well as families with children.

Oldest Cities in the US – San Francisco, California

Founded: 1776

History of San Francisco:

San Francisco was founded by colonists from Spain. The California gold rush starting in 1848 led to a large boom in population, including considerable immigration which made San Francisco the most rapidly growing city in the U.S. During the 1860s to the 1880s San Francisco began to transform into a major city. However, later three-quarters of the city was destroyed in the earthquake and subsequent fire of 1906. After World War II, San Francisco became a magnet for America’s counterculture and became world-famous for the Summer of Love.

Where to go in San Francisco:

San Francisco is on the American bucket list, because it has many beautiful locations and every single one of them is worth going to. If you are interested in an excellent view of the Golden Gate Bridge then there are two really great spots. First is a walk along the coast of the Marina District, a beautiful row of multi-million-dollar houses will be on your left and eventually you will see the Wave Organ on your right.

Another one is next is Sutro Heights park, here you can walk through several beautiful trails and get another wonderful view of the Golden Gate bridge (Lands End Labyrinth is also located here). If you enjoy shopping more then Union square is an excellent location for you. Chinatown is just two blocks north as well and is a perfect location to bring back souvenirs for the family.

Finally, you can’t talk about San Francisco without mentioning Fishermans Wharf. Located right next to Pier 39 (another great spot where the famous Sea Lions are located). If you enjoy freshly caught sea food and outdoor bars with happy hours then this is the place for you. Beware though, the crowds can be much more dense here so going during less busy hours could be a good strategy.

San Francisco Tip:

Make sure and plan your routes in advance if you are going to walk around the city. A big mistake we made on our first day was going straight from point A to point B. We quickly discovered exactly how steep the hills were. A little extra walking around the hills can mean a lot less effort and significantly less sore legs at the end of the day. For more San Francisco tips, check out my guide on San Francisco.

Oldest Cities in the US – Washington D.C.

Founded: 1790

History of Washington D.C.: Founded on July 16, 1790, Washington, DC is unique among American cities because it was established by the Constitution of the United States to serve as the nation’s capital. As a result, Washington became both a center of African American culture and a center of Civil Rights Movement.

Where to Go in Washington D.C.

Washington, D.C. is one of the most tourist-friendly cities in the United States as most attractions are free. The city is home to all three branches of the federal government, as well as the White House, the Supreme Court and the Capitol Building. Visit the sites of later forts from the Civil War at the Fort Circle Parks, then take a tour of the White House built in the late 1700’s, the United States Capitol building from 1800, and the Washington Monument, built in 1885.

Traveler’s Tip: Every trip on the Metro is an extra $1 using a paper ticket, so unless you’re planning only a couple of rides, a SmarTrip card will be best. You can buy one at any Metro station.

Tell me: What are your favorite oldest cities in the US that you visited? Let me know in the comments below which cities you enjoyed!