Oldest City

St. John's
Ok this one has a lot of controversy surrounding it. There's 2 different historic versions of this fact and one says it was St. John's, Newfoundland that was the oldest but considering St. John's was not considered a part of Canada until late 1800's to 1900's that makes it hard to believe.

Quebec City
Quebec City lays the claim to being the oldest city because it was founded in 1608 and has always been considered a part of Canada. You be the judge!
Oldest National Park

The oldest national protected park in Canada is Banff in Alberta. The park was founded in 1885 and has been one of Canada's most recognized places. The park is still open and is amazing to visit.
Oldest Corporation/Company

The oldest trading company/corporation in Canada and the entire world is the “Hudson's Bay Company” which was established in 1670. To this day the company is still operational and remains the power house of all companies. Although a few years back an American bought the company.
Oldest Airline

The oldest airline in Canadian history is the “Austin Airways” which was originally started in 1934. Through out the years, the airline company merged with a few different airlines but always used their own name. As of 2001 Austin Airways once again merged and is now apart of “Air Canada Jazz” and still does passenger flights to this day.
Oldest Golf Course

Perth Golf Course

Royal Montreal Golf Course
Again there's a lot of controversy in this fact but never the less here it is. First is Perth golf course in Ontario. It started in 1890 and is known as the oldest permanent golf course in Canada. Others claim the actual oldest golf course is really the “Royal” Montreal Golf Club which was founded way back in 1873. No matter which is the oldest, both courses are still open to play at.
Oldest Microwave

Now almost everyone in the world owns a microwave but how many of us can say “I'm still using the first one I bought”. Well one resident in Etobicoke, Ontario was discovered to have the oldest working microwave in Canada. Isabelle Cadel had bought her microwave new in the summer of 1952 and still uses it to this day. At the time of purchase the appliance was the newest and most advanced of its time.
Oldest Woman's Magazine

Canada's oldest woman's magazine is “Chatelaine” which started to publish their magazines in 1929. This is one of the more popular Canadian magazines with an estimated 4.4 million readers and still being published to this day.
Oldest Skateboard Shop

Alright this one is for all you skateboard fans. Canada's oldest skateboard shop is “PD's Hot Shop” which was first opened in 1976. The shop has been serving its skateboarding fans ever since and is now located on the Westside of Vancouver, British Columbia.
Oldest Western Newspaper

Now again this is only the oldest newspaper in Western Canada not to be confused with the first Canadian newspaper “Halifax Gazette”. The “Winnipeg Free Press” has been operating since 1872 and is located in Winnipeg, Manitoba. The paper is still in circulation to this day.
Oldest Reward Program

Well anyone living in Canada knows about the infamous Canadian Tire money which is Canada's oldest reward program. The program works like this: after you purchase gas or any products from any Canadian Tire, then the teller gives you your change and so much Canadian Tire money depending how much you spent. It takes awhile to build up a good amount of Canadian Tire money but once you do, you're free to go buy anything in any of their stores. Program came into effect in Toronto in 1958 and has been going strong ever since. There are now over 200 gas bars and over 432 Canadian Tire's all over Canada.
Oldest University

The oldest Canadian university I could find in the history books was the “Universite Laval” in Quebec which is the 5 th oldest university in the Americans. It first opened it doors to students on December 8, 1852 and as far as I know is still operational to this day.
Oldest and Largest Public Market

Growing up in Ottawa as a young boy I know all to well about this market and have been their many times when I was a child. The market is known as the “Byward Market” which was established in 1826 in downtown Ottawa. To this day on any weekend if you travel down to the heart of Ottawa, you cannot miss the Byward Market.
Oldest Private Zoo

Finally we come to Canada's oldest known private zoo called the “Bomanville Zoo” which is of course located in Bomanville, Ontario. It was first opened in 1919 and has over 300 creatures for people to see. To this day the Bomanville zoo is still one of the largest attractions in the city.
Well that's about it but please keep in mind that all facts I found were researched and should be correct but also remember I can only provide the information I can find online or personally know. So if anyone has disagreements with any fact listed here please feel free to comment but PLEASE keep ignorant remarks to yourself.