There are two answers.
Edmonton became a permanent settlement in 1811. Before 1811, there were three different "Fort Edmonton"'s. The first was in today's Fort Saskatchewan; the second was in Edmonton but closed after a few years; the third was near Smoky Lake, along the North Saskatchewan River about a hundred kilometres east of Edmonton. But since 1811 there has not been a time that people have not lived in Edmonton. It became a town in 1892 and a city in 1904, later incorporating one other city (Strathcona), two villages and two towns.
Calgary became a permanent settlement in 1873, when the first recorded settler John Glenn established a pioneer combination farm/ranch/trading post/stopping house on the site of the present city. Its prominence was established when the North-West Mounted Police founded a post on the site in 1875 and further entrenched when the CPR came through in 1883. it became a town in 1884 and a city in 1893.
The oldest (known) settled place in Alberta appears to be a tie - Fort Chipewyan and Fort Vermilion.
Fort Chipewyan is on the shores of Lake Athabasca. This present-day hamlet of about 800 residents got its known start in 1788 when Peter Pond of the North West Company founded a fur-trading post there, probably near the site of an established Native campsite.
Fort Vermilion is on the banks of the Peace River. It was also founded in 1788. It was established as a fur-trading post by the North West Company just upstream of the unpassable Vermilion Chutes rapids. Today, Fort Vermilion, a hamlet located southeast of High Level, serves an urban and rural population of about 2,500.
The oldest building still standing in its original location
At Victoria Settlement, an historic site surrounded by working farms and residences located 90 kms northeast of Edmonton, sits a building that is the oldest building still surviving and sitting on its original site. The clerks' quarters building of the old fur trading post was built in 1865. The Hudson's Bay Company opened Fort Victoria in 1864 to access furs harvested by Cree in the area. It was located along the North Saskatchewan River, the main transportation route of the time, to allow ease of import and export. In its 30-plus years of somewhat-intermittent operation, it gave its name to the section of the Edmonton-Carlton Trail that wound past its palisade walls. The name Victoria Trail is still used for the paved road that now overlays the old Red River cart trail in the area and is also used for an Edmonton road similarly built on a section of the old "Carlton Trail." The fort was named after Queen Victoria, who reigned from 1837 to 1901.
Although miniscule by today's standards, its local importance and its historicity led to the name "Victoria" being used into the 1930s for provincial and federal electoral districts that enclosed the post and the settlement that grew around it. (info taken from Peter Melnycky's book, A Veritable Canaan, Alberta's Victoria Settlement (1997)).
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