Oldest Cities in America: Awesome Guide!

Written by Town & Tourist

What better vacation destinations for a U.S. history buff to travel to than the 16 oldest cities (continuously inhabited) in the United States? Here is a brief history of the oldest cities in America and links to discover things to do in each of these historic old cities.

The Oldest Cities in America

Saint Augustine, Florida

Founded: 1565

Then: St. Augustine, Florida, located 38 miles southeast of Jacksonville, is the oldest continuously settled city (by Europeans) in the United States. The Spanish explorer, Juan Ponce de Leon, in search of the legendary Fountain of Youth, landed there in 1513 and took possession of the territory for Spain.

Prior to the founding of St. Augustine in 1565, several earlier attempts at European colonization were made by both Spain and France, but all failed.

The tall ship El Galeón is a replica of a Spanish galleon from the colonial period. El Galeón is an occasional visitor to St. Augustine and when docked here, it is open daily allowing guests to freely roam the deck as well as the decks below.

Ships such as this one sailed Florida’s coastal waters during the 16th and 17th centuries, crossing the ocean from the Old World to the New for trade and exploration purposes.

El Galeón

El Galeón is a 1/1 scale reconstruction of a 16th Century Spanish galleon. | Img Src:

Now: Since the late 19th century, St. Augustine’s distinct historical character has made the city a major tourist attraction. Today the city of St. Augustine is a popular travel destination and is a well-preserved example of Spanish-style buildings and 18th- and 19th-century architecture.

St. Augustine is a very walkable city, with several oceanfront parks and a mild subtropical climate that allows for a 12-month tourist season.

The heart of the city is its Historic District, the oldest part of the city with many buildings dating back to the 1700s. Here, you will find a majority of the city’s restaurants, shopping, hotels, and attractions. The Historic District is very walkable and is home to the beautiful bayfront with lovely panoramic views of the Matanzasa Bay.

If you visit during December or January, you are in for a special treat with the famous St. Augustine Nights of Lights holiday display.

Nights of Lights, St. Augustine, Florida

Nights of Lights, St. Augustine, Florida

One look and you will understand why St. Augustine’s Nights of Lights was twice selected by National Geographic as one of the ten best holiday lighting displays in the world.

Rachel Ray Magazine named St. Augustine one of the Nation’s “Twinkliest Towns” and the American Business Association named the Nights of Lights a Top 100 Event in North America.

From the end of November through the end of January, the 144-square-block historic district twinkles with two million bulbs (each white, per city ordinance).

For more on St Augustine check out:

Epic Weekend in St Augustine: Family Guide!

St Augustine: Ultimate Nightlife Guide

St Augustine Nightlife guide

St Augustine Nightlife guide. Source:

St Augustine Wild Reserve in Florida: 5 Reasons to Visit!

St Augustine Wild Reserve Tours

St Augustine Wild Reserve Tours

Source: Wiki

Jamestown, Virginia

Founded: 1607

The Jamestown settlement in the Colony of Virginia was the first permanent English settlement in the Americas. Jamestown was established by the Virginia Company of London as “James Fort” in May 1607 and was considered permanent after brief abandonment in 1610. It followed several earlier failed attempts, including the Lost Colony of Roanoke.

The Replica "Godspeed" from Jamestown, VA

The Replica “Godspeed” from Jamestown, VA | Img Src:

In the present time, Jamestown is home to two heritage tourism 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.

Check out the hidden gem: 24 Hours in Richmond, Virginia: One Day Itinerary

Source: Wikipedia

Santa Fe, New Mexico

Founded: 1607

Santa Fe, New Mexico, was occupied for at least several hundred years by indigenous peoples before the city of Santa Fe was founded by Spanish colonists in 1610.

In 1912, New Mexico was admitted as the United States of America’s 47th state, with Santa Fe as its capital. Sante Fe is known as the oldest state capital city in the United States and the oldest city in New Mexico.

Most tourist activity takes place in the historic downtown, especially on and around the Plaza, a one-block square adjacent to the Palace of the Governors, the original seat of New Mexico’s territorial government since the time of Spanish colonization.

Other areas include “Museum Hill”, the site of the major art museums of the city as well as the Santa Fe International Folk Art Market, which takes place each year during the second full weekend of July. The Canyon Road arts area with its galleries is also a major attraction for locals and visitors alike.

Some visitors find Santa Fe particularly attractive around the second week of September when the aspens in the Sangre de Cristo Mountains turn yellow and the skies are clear and blue.

This is also the time of the annual Fiestas de Santa Fe, celebrating the “reconquering” of Santa Fe by Don Diego de Vargas, a highlight of which is the burning Zozobra (“Old Man Gloom”), a 50-foot (15 m) marionette.

The Official Burning of Zozobra, Sante Fe, NM

The Official Burning of Zozobra, Sante Fe, NM

Source: Wiki

Hampton, Virginia

Founded: 1610

Hampton traces its history to the city’s Old Point Comfort, the home of Fort Monroe for almost 400 years, which was named by the 1607 voyagers, led by Captain Christopher Newport, who first established Jamestown as an English colonial settlement. Source: Wiki

Blackbeard Pirate Festival

Blackbeard Pirate Festival

Once a year visitors from all over the country enjoy the sights and sounds of 18th century Hampton overrun by pirates when Hampton’s waterfront comes alive during the Blackbeard Pirate Festival.

The festival features dozens of pirate re-enactors, costumed in historically accurate garb, who transform today’s Hampton into the busy seaport of yesterday.

Led by Blackbeard the Pirate himself, re-enactors help visitors step back in time and re-live the history and legends of 1718 Hampton.

Kecoughtan, Virginia

Founded: 1610

Map depicting the Colony of Virginia (according to the Second Charter), made by Willem Blaeu between 1609 and 1638

Map depicting the Colony of Virginia. (1609-1638)

Kecoughtan, a better-sited location in the present-day independent city of Hampton, was essentially stolen from Native Americans in 1610 by the English colonists, under the leadership of Sir Thomas Gates.

In the 21st century, through the old American Indian village of Kecoughtan, the City of Hampton lays claim to status as the oldest continually occupied settlement in the British Colonies in what is now the United States. Source: Wiki

Newport News, Virginia

Founded: 1613

The harbor area of Hampton Roads, from official state map of pre-civil war Virginia circa 1858.

The harbor area of Hampton Roads. (c. 1858)

During the 17th century, shortly after founding of Jamestown, Virginia in 1607, English settlers explored and began settling the areas adjacent to Hampton Roads.

In 1610, Sir Thomas Gates “took possession” of a nearby Native American village, which became known as Kecoughtan.

At that time, settlers began clearing land along the James River (the navigable part of which was called Hampton Roads) for plantations, including the present area of Newport News. Source: Wiki

Albany, New York

Founded: 1614

N. Pearl St. from Maiden Ln. North. (c. 1805)

N. Pearl St. from Maiden Lane North, circa 1805

Albany is one of the oldest surviving European settlements from the original thirteen colonies and the longest continuously chartered city in the United States. The Hudson River area was originally inhabited by Algonquian-speaking Mohican (Mahican), who called it Pempotowwuthut-Muhhcanneuw, meaning “the fireplace of the Mohican nation.” It is likely the Albany area was visited by European fur traders, perhaps as early as 1540, but the extent and duration of those visits has not been determined. Source: Wiki

Jersey City, New Jersey

Founded: 1617

Jersey City at the end of the 19th century

Jersey City at the end of the 19th century

The land comprising what is now Jersey City was inhabited by the Lenape, a collection of tribes (later called Delaware Indian).

In 1609, Henry Hudson, seeking an alternate route to East Asia, anchored his small vessel Halve Maen (English: Half Moon) at Sandy Hook, Harsimus Cove and Weehawken Cove, and elsewhere along what was later named the North River.

After spending nine days surveying the area and meeting its inhabitants, he sailed as far north as Albany. Source: Wiki

Plymouth, Massachusetts

Founded: 1620

The First Thanksgiving, painted by Jean Leon Gerome Ferris (1863–1930). The First Thanksgiving took place in Plymouth in 1621.

The 1st Thanksgiving was in Plymouth in 1621.

As one of the country’s first settlements, Plymouth is well known in the United States for its historical value.

The events surrounding the history of Plymouth have become part of the ethos of the United States, particularly that relating to Plymouth Rock, the Pilgrims, and the First Thanksgiving.

The town itself is a popular tourist spot during the Thanksgiving holiday. Pictured: The First Thanksgiving, painted by Jean Leon Gerome Ferris (1863–1930). Source: Wiki

Weymouth, Massachusetts

Founded: 1622

First Weymouth Town Hall. It was built 1852 and destroyed by fire in 1914.

First Weymouth Town Hall. (1852-1914)

The site of Weymouth first saw European inhabitants in 1622 as Wessagusset Colony, a colony founded by Thomas Weston, who had been the main backer of the Plymouth settlement.

The settlement was a failure. The sixty men taken from London were ill-prepared for the hardships required for survival.

They also may have lacked the motivation of the Pilgrims as this colony was purely economic in motivation and the men had not brought their families.

Ten of the original sixty starved to death, five were killed in conflict with the Natives, and the remainder joined Plymouth or went north to Maine, and from there most returned to England. A new colony was formed at the site later that year. Source: Wikipedia

Dover, New Hampshire

Founded: 1623

Raid on Dover

Raid on Dover

In 1623, William and Edward Hilton settled Cochecho Plantation, adopting its Abenaki name, making Dover the oldest permanent settlement in New Hampshire. On June 28, 1689, Dover suffered a devastating attack by Indians.

It was revenge for an incident on September 7, 1676, when 400 braves were duped by Major Richard Waldron and were mostly either hung or sold into slavery.

Thirteen years passed. When colonists thought the episode was forgotten, they struck. Fifty-two colonists, a quarter of the population, were either captured or slain. Source: Wikipedia

Gloucester, Massachusetts

Founded: 1623

Man at the Wheel, Fisherman's Memorial Cenotaph

Man at the Wheel, Fisherman’s Memorial

Gloucester was founded at Cape Ann by an expedition called the “Dorchester Company” of men from Dorchester (in the county of Dorset, England) chartered by James I in 1623.

It was one of the first English settlements in what would become the Massachusetts Bay Colony, and predates both Salem in 1626 and Boston in 1630.

The first company of pioneers made landing at Half Moon Beach and settled nearby, setting up fishing stages in a field in what is now Stage Fort Park. This settlement’s existence is proclaimed today by a memorial tablet, affixed to a 50-foot (15 m) boulder in that park.

Life in this first settlement was harsh and it was short-lived. Around 1626 the place was abandoned, and the people removed themselves to Naumkeag (what is now called Salem, Massachusetts), where more fertile soil for planting was to be found.

The meetinghouse was even disassembled and relocated to the new place of settlement. At some point in the following years – though no record exists – the area was slowly resettled. The town was formally incorporated in 1642. Source: Wiki

New Amsterdam, New York

Founded: 1625

1882 depiction of the ship Mayflower sailing from England to America in 1620, in Plymouth Harbor

Depiction of the ship Mayflower in 1620

New Amsterdam was a 17th-century Dutch settlement established at the southern tip of Manhattan Island that served as the seat of the colonial government in New Netherland.

In 1624, it became a provincial extension of the Dutch Republic and was designated as the capital of the province in 1625.

New Amsterdam was renamed New York on September 8, 1664, in honor of the Duke of York (later James II of England), in whose name the English had captured it. (Note: In 1620 the Pilgrims attempted to sail to the Hudson River from England.

However, the Mayflower reached Cape Cod (now part of Massachusetts) on November 9, 1620, after a voyage of 64 days. For a variety of reasons, primarily a shortage of supplies, the Mayflower could not proceed to the Hudson River, and the colonists decided to settle near Cape Cod, establishing the Plymouth Colony. Source: Wiki

Salem, Massachusetts

Founded: 1626

Scene along the Salem waterfront, circa 1770–80

Scene along the Salem waterfront, circa 1770–80

Salem is located at the mouth of the Naumkeag river at the site of an ancient American Indian village and trading center. It was first settled by Europeans in 1626 and originally included much of the North Shore, including Marblehead.

Puritans had come to Massachusetts to obtain religious freedom for themselves, but had no particular interest in establishing a haven for other faiths.

Much of the city’s cultural identity reflects its role as the location of the infamous Salem witch trials of 1692, as featured in Arthur Miller’s The Crucible.

Tourists know Salem as a mix of important historical sites and a vibrant downtown that has more than 60 restaurants, cafes, and coffee shops. In 2012, the Retailers Association of Massachusetts chose Salem for their inaugural “Best Shopping District” award. More than one million tourists from all around the world visit Salem annually, bringing in at least $100 million in tourism spending each year. Salem is one of the most popular places to visit for Halloween and more than 250,000 people visited Salem during Halloween weekend in 2016.

Source: Wiki

Lynn, Massachusetts

Founded: 1629

Aerial Illustration of Lynn, c. 1881

Aerial Illustration of Lynn, c. 1881

Prior to European colonization, the area today known as Lynn was inhabited by the Naumkeag people. European settlement of the area was begun in 1629. A noteworthy early Lynn colonist, Thomas Halsey, left Lynn to settle the East End of Long Island, where he founded the Town of Southampton, New York.

The resulting Halsey House—the oldest extant frame house in New York State (1648)–is now open to the public, under the aegis of the Southampton Colonial Society.

Lynn was long colloquially referred to as the “City of Sin,” owing to its historic reputation for crime and vice. Today, however, the city is known for its large international population, historic architecture, downtown cultural district, loft-style apartments, and public parks and open spaces. Source: Wiki

Charlestown, Massachusetts

Founded: 1629

Charlestown's former City Hall

Former City Hall

Charlestown is the oldest neighborhood in Boston, Massachusetts. It is located on a peninsula north of the Charles River, across from downtown Boston, and also adjoins the Mystic River and Boston Harbor.

Charlestown was laid out in 1629 by engineer Thomas Graves, one of its early settlers, in the reign of Charles I of England.

It was originally a separate town and the first capital of the Massachusetts Bay Colony. Source: Wikipedia

We would love to hear about your trip to these oldest cities in America! Please tell us in the comments below what you enjoyed most about your visit and what you would recommend that others experience in these oldest cities in our country.

Be sure to check out:

Epic Weekend in St Augustine: Family Guide!

Pirate Tour St Augustine

Pirate Tour St Augustine

St Augustine: Ultimate Nightlife Guide

Colonial Quarter St Augustine

Colonial Quarter St Augustine. The multiple flags represent the vast number of European Colonials which occupied St Augustine.


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Town & Tourist

A travel resource guide that has been carefully crafted and curated by travel bloggers to help you find the best places to travel to in the USA.