St. John’s, NL (No. 1)
St. John's is the capital and largest city in Newfoundland and Labrador, Canada. St. John's was incorporated as a city in 1888, yet is considered by some to be the oldest English-founded city in North America. It is located on the eastern tip of the Avalon Peninsula on the island of Newfoundland.
St. John's is one of the oldest settlements in North America, with year-round settlement beginning sometime after 1630 and seasonal habitation long before that. It is not, however, the oldest surviving English settlement in North America or Canada. Sebastian Cabot declares in a handwritten Latin text in his original 1545 map, that the St. John's earned its name when he and his father, the Venetian explorer John Cabot became the first Europeans to sail into the harbour, in the morning of 24 June 1494 (against British and French historians stating 1497), the feast day of Saint John the Baptist. However, the exact locations of Cabot's landfalls are disputed. A series of expeditions to St. John's by Portuguese from the Azores took place in the early 16th century, and by 1540 French, Spanish and Portuguese ships crossed the Atlantic annually to fish the waters off the Avalon Peninsula. In the Basque Country, it is a common belief that the name of St. John's was given by Basque fishermen because the bay of St. John's is very similar to the Bay of Pasaia in the Basque Country, where one of the fishing towns is also called St. John (in Spanish, San Juan, and in Basque, Donibane). The earliest record of the location appears as São João on a Portuguese map by Pedro Reinel in 1519.
Source: Wikipedia