What is the oldest city in the US? Photo: New York Times
What is the oldest city in the US? Photo: New York Times

Which Is The Oldest City In America

The Roanoke colony was established in 1585, Jamestown in 1607. The pilgrims landed at Plymouth Rock in 1620. While all of these events are an important part of the nation's beginnings, none of them marked the first permanent settlement in what would later become the United States. That distinction belongs to St. Augustine, Florida, established by the Spanish in 1565.

St. Augustine, founded in September 1565 by Don Pedro Menendez de Aviles of Spain, is the longest continually inhabited European-founded city in the United States – more commonly called the "Nation’s Oldest City."

History of St. Augustine

Photo: Time Out
Photo: Time Out

Historians credit Juan Ponce de Leon, the first governor of the Island of Puerto Rico, with the discovery of Florida in 1513. While on an exploratory trip in search of the fabled Bimini he sighted the eastern coast of Florida on Easter Sunday, which fell on March 27 that year. Ponce de Leon claimed Florida for the Spanish Crown and named it Florida after the Easter season, known in Spanish as Pascua Florida. This newly claimed territory extended north and west to encompass most of the known lands of the North American continent that had not been claimed by the Spanish in New Spain (Mexico and the Southwest).

In the following half century, the government of Spain launched no less than six expeditions attempting to settle Florida; all failed. In 1564 French Huguenots (Protestants) succeeded in establishing a fort and colony near the mouth of the St. Johns River at what is today Jacksonville. This settlement posed a threat to the Spanish fleets that sailed the Gulf Stream beside the east coast of Florida, carrying treasure from Central and South America to Spain. As Don Pedro Menéndez de Avilés was assembling a fleet for an expedition to Florida, the French intrusion upon lands claimed by Spain was discovered. King Philip II instructed Menéndez, Spain's most capable admiral, to remove the French menace to Spain's interests.

On September 8, 1565, with much pomp and circumstance and 600 voyagers cheering, Menéndez set foot on the shores of Florida. In honor of the saint whose feast day fell on the day he first sighted land, Menéndez named the colonial settlement St. Augustine. Menéndez quickly and diligently carried out his king's instructions. With brilliant military maneuvering and good fortune, he removed the French garrison and proceeded to consolidate Spain's authority on the northeast coast of Florida. St. Augustine was to serve two purposes: as a military outpost, or Presidio, for the defense of Florida, and a base for Catholic missionary settlements throughout the southeastern part of North America.

The Treaty of Paris in 1763, ending the French and Indian War, gave Florida and St. Augustine to the British, accomplishing by the stroke of a pen what pitched battles had failed to do. St. Augustine came under British rule for the first time and served as a Loyalist (pro-British) colony during the American Revolutionary War. A second Treaty of Paris (1783), which gave America's colonies north of Florida their independence, returned Florida to Spain, a reward for Spanish assistance to the Americans in their war against England.

During what is called by historians the Second Spanish Period (1784 to 1821), Spain suffered the Napoleonic invasions at home and struggled to retain its colonies in the western hemisphere. Florida no longer held its past importance to Spain. The expanding United States, however, regarded the Florida peninsula as vital to its interests. It was a matter of time before the Americans devised a way to acquire Florida. The Adams-Onîs Treaty, negotiated in 1819 and concluded in 1821, peaceably turned over the Spanish colonies of East and West Florida and, with them, St. Augustine, to the United States.

Twenty years after the end of the Civil War, St. Augustine entered its most glittering era. Following a visit to the crumbling old Spanish town, Henry Flagler, a former partner of John D. Rockefeller in the Standard Oil Company, decided to create in St. Augustine a winter resort for wealthy Americans. He owned a railroad company that in 1886 linked St. Augustine by rail with the populous cities of the east coast. In 1887, his company began construction of two large and ornate hotels and a year later added a third that had been planned and begun by another developer. Flagler's architects changed the appearance of St. Augustine, fashioning building styles that in time came to characterize the look of cities throughout Florida. For a time, St. Augustine was the winter tourist mecca of the United States.

The city celebrated its 400th anniversary in 1965 and undertook in cooperation with the State of Florida a program to restore parts of the colonial city. The continuation of an effort actually begun in 1935, what became known as the "Restoration" resulted in preserving the thirty-six remaining buildings from the colonial era and the reconstruction of some forty additional colonial buildings that had previously disappeared, transforming the appearance of the historic central part of St. Augustine. It was in great part a tribute to such efforts that King Juan Carlos and Queen Sofia made this small city a part of their 2001 visit to the United States.

Highlighted places to see in St. Augustine - the first city in America

1. El Galeon Andalucia

Photo: Tall Ships Network
Photo: Tall Ships Network

The Galeon Andalucia is a replica ship built in 2009 modeled after the type of vessel used by the Spanish Crown for maritime expeditions during the 16th through the 18th centuries. Galleons were intended to discover and then establish trade routes between Spain, America and the Philippines islands. These merchant vessels were armed with tonnages ranging from 500 to 1,200 and lengths ranging from 130 to 200 feet. Considered innovative for their time, they were designed to cross the largest oceans as efficiently as possible.

Since her launching, a crew of fifteen to thirty-five people have manned her across the seas and oceans of the world. She has navigated the Pacific and Indian Oceans, crossed the Atlantic, and traveled the Mediterranean Sea, the Red Sea, the South and East China Seas, the Aegean Sea and the Caribbean.

Some facts about the El Galeon Andalucia:

Fifty-ton Spanish galleon

164 feet length, overall

33 foot main beam

10.5 foot draft

Four masts hold six sails measuring almost 11,000 square feet

Average speed - 7 knots

Crew size - 15-35 people

2. Castillo de San Marcos

Photo: Visit St. Augustine
Photo: Visit St. Augustine

Perhaps the fort’s air of authority comes from the Castillo’s sheer size. The building’s shell alone is as big as a city block, and its site occupies more than 20 acres along the downtown corridor. Nowhere else in Florida can you see, feel and comprehend the critical role played by this little city during the years when West European countries battled each other over the Atlantic Coast in the New World. Inside the fort, visitors can investigate the many rooms of the fort’s first level—including a chapel and a single cell used as the city’s first jail—and see a video about the Castillo’s significance. But the true wonder of this fort can be experienced on the second level, where expansive views of St. Augustine, up-close looks at the towers where soldiers once stood guard and cannon demonstrations bring the fort to life.

3. Fountain of Youth

Photo: Visit St. Augustine
Photo: Visit St. Augustine

The Fountain of Youth Archaeological Park is a 15-acre, waterfront historical attraction, where visitors can learn about the first Spanish settlers who came here in the 1600s and the native Timucuans who were here to greet them. With a working archaeological dig on site, as well as several re-created Spanish and Timucuan buildings and dwellings, the park is bursting with history.

It's also just a beautiful spot to relax, enjoy the views over the water from the 600-foot Founders Riverwalk or from the Observation Tower, sample the waters from the natural spring (Ponce de Leon's legendary Fountain of Youth?), and let the kids feed the roaming peacocks.

The Fountain of Youth offers a variety of shows and living history reenactments designed to entertain and educate visitors -- the Planetarium, the two-story Discovery Globe mapping the routes of the early explorers, the Timucuan Village, and the reconstructed First Mission of Nombre de Dios.


Head just out of town to explore 42 miles of pristine Atlantic beaches, where you can swim, surf, or just kick back on the sand.

While you’re there, make sure to visit the historic 1874 St. Augustine Lighthouse, a stately black and white sentinel at the nation’s oldest port. If you want to feel the burn and snag a unique view of the area at the same time, you can climb the 219 steps to reach the observation deck of the 165-foot-tall Lighthouse. Hands-on exhibits, daily programs, and nature trails round out the fun.

4. Lightner Museum

Photo: Visit St. Augustine
Photo: Visit St. Augustine

The Lightner Museum offers visitors an immersive experience of art, architecture, and history.

Founded by Chicago Publisher Otto Lightner in 1948, today the museum presents Lightner's unique collection of Americana, fine and decorative art, and natural history specimens, alongside compelling exhibitions and programs.

The museum is housed in the former Alcazar Hotel. Built in 1888 by Henry Flagler, the Alcazar was the railroad magnate’s second grand hotel in St. Augustine. Designed by the firm of Carrère and Hastings, the Spanish Renaissance Revival hotel hosted thousands of guests who enjoyed its remarkable recreation facilities — including the world's largest swimming pool, Turkish and Russian steam baths, tennis courts, and a gymnasium. The Alcazar closed during the Depression and the former Gilded Age resort hotel was transformed into an eclectic museum of art and artifacts by Otto Lightner.

Today, the heart of the Lightner Museum is its diverse and extraordinary collection, including lamps by Louis Comfort Tiffany, 19th century American and European paintings, geological specimens and shells collected from all over the globe, and mechanical musical instruments of the Victorian era.

St. George Street and nearby

St. George Street also offers attractions, including the Medieval Torture Museum, which promises to “transport you back in time hundreds of years to some of the most miserable moments in human history.” The museum highlights methods of medieval torture through displays, props, and mannquin; while it’s fascinating and unique, it’s not for kids or those prone to nightmares.

Save time for areas close to St. George Street. Hypolita Street, Cuna Street, Cathedral Place and King Street are home to still more shops and restaurants, particularly near Casa Monica Hotel, a magnificent structure with a storied past.

If you’re looking for a quieter alternative, Aviles Street, which holds bragging rights as the oldest street in the United States, features a quaint neighborhood complete with cobblestone streets, highlighted with shops, cafes, historic sites, and galleries chock-full of original art.

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