This answer will give both the modern sense of a city and the classic definition as well. In modern times cities are founded by documents that incorporate them, while in older times cities were founded by a group of people calling a group of homes by a name to define it.
Classical sense (may still be occupied and in use):
700 B.C. Ticul* - Still occupied today, founded by Mayans - Central Mexico
650 A.D. Cahokia - unoccupied, founded by the Mound Builders - United States
1000 A.D. Oraibi - Occupied, founded by the Hopi - (Arizona) United States
1000 A.D. Taos Pueblo - Continuously occupied, built by the Puebloan people - (New Mexico) United States
1003 A.D. L'Anse aux Meadows - unoccupied founded by the Norse (European) - Canada
Modern sense (requires foundational charter or incorporation paperwork)
1498 A.D. Santo Domingo* - founded by Spanish Charter - Dominican Republic
1510 A.D. Nombre de Dios - Spanish Charter - Panama
1521 A.D. San Juan - Spanish Charter - Puerto Rico, United States
1565 A.D. St. Augustine - Spanish Charter - Florida, United States
1583 A.D. St. John's Newfoundland - British Charter - Canada
* NOTE: These cities were originally cities by indigenous populations that were either re-occupied or taken over by settlers.
Some of these cities are noted for their historical significance. Oraibi for instance is still occupied today by indigenous populations. L'Anse aux Meadows was the first European city in the Americas, founded by Lief Ericson, and although the colony failed it was the first.
The other cities are listed to include definitions originally debated in this answer (the islands part of North America vs. the main continent).
Top 10 largest US cities in square miles:
1. Sitka, Alaska (4811.5)
2. Juneau, Alaska (3255)
3. Anchorage, Alaska (1697.2)
4. Jacksonville, Florida (757.7)
5. Anaconda, Montana (741)
6. Butte-Silver Bow, Montana (719)
7. Willow, Alaska (684.8)
8. Healy, Alaska (669)
9. Oklahoma City (607.0)
10. Houston (579.4) 27. New York (54556). This figure includes the Appalachian Valley, Adirondack Mountains, Allegheny Plateau and other mountains, lakes, forests, rivers and farms which cover most of New York (northern, eastern, western, central and a bit of southern). It is the rural/suburban area of New York and is also called "Upstate New York". However, "Downstate New York", the urban area, or more commonly known as New York City measures only 304.8 square miles, which is why New York is 27th instead of 1st.
The oldest continuously occupied European settlement in North America is though to be Saint Augustine, which is a Spanish settlement in Florida. However there was an earlier settlement by the Norse, L'Anse aux Meadows in Newfoundland. It dates back to the 10th century, where Columbus came into the picture in the late 15th century.
St. John's, Newfoundland and Labrador is the oldest city in Canada, although the oldest incorporated city, is Saint John, New Brunswick.
St. John's, Newfoundland is the oldest city in Canada, established in 1583.
saint john new brunswick
Jerusalem would be one of the oldest cities.
australias oldest and youngest capital cities
asian bussnispeople have brought a great deal of welth to canadas economy
No the oldest part of london is its cities
your answer is Jericho.
no, it is one of the oldest inhabited cities in the world thou
indraprastha
Damascus
Nacadoches Victoria Goliad
Chester, PA
Athens is typically regarded as Europe's oldest city.
Matera is the oldest city in Italy, and one of the five oldest cities in the world.