Perimeter Aviation was started in 1960 by William (Bill) J. Wehrle, as Canada's first private Instrument Flight Rating (IFR) School.

In 1964 Perimeter bought their first hangar at the Winnipeg International Airport to start servicing aircraft, and acquired a Beech 18 to begin flying charters.

By 1967 company offerings included a flight school, charter services, and an aircraft maintenance facility.

1976 was an important year for Perimeter. The company was approached by Transair to purchase their northern interior flight routes along with two Twin Otter aircraft, which resulted in instant growth, forcing the company to expand from 25 employees to 100 almost overnight.

In 1977 Perimeter expanded into the executive jet market by purchasing a Lear 35. The company also purchased a King Air 100, Beech Duke and Beech Baron in 1977 to bolster it's aircraft offerings for the charter market. 

In 1978 Perimeter purchased two brand-new Metro aircraft to provide scheduled passenger flight to Brandon, Dauphin, Yorkton and Saskatoon.

In 1980 Perimeter bought three Beech Baron aircraft to fly "bag runs" to communities in Manitoba and Northern Ontario, which are still being operated today.

In 1985 Perimeter expanded its Metro fleet and started providing flight services to northern communities.

In 1991 Perimeter completed construction of a new cargo building beside their terminal and hangar facilities in Winnipeg, MB to support their cargo shipping business segment.

Throughout the 90's Perimeter continued to grow, which included the addition of a hangar for the training school, and various aircraft to support expanding scheduled passenger services to communities in Manitoba and Northern Ontario.

In 1997 the company received authorization from Transport Canada to overhaul Garrett turbine engines to zero-time, making them the only company in Canada with authorization to do this kind of work on Garrett turbine engines.

In 2001, Perimeter started a full-time dedicated Aeromed air ambulance emergency evacuation service for communities in Manitoba, with the capability of providing Aeromed charter services to anywhere in North America.

In May 2004, Perimeter Aviation was acquired by Exchange Income Corporation (EIC); a Canadian corporation created to invest in profitable, well-established companies with strong cash flows operating in niche markets in Canada and/or the United States and to distribute stable monthly cash dividends to its shareholders. Perimeter is one of several airlines owned by EIC, the others being Calm Air, Keewatin Air, Bearskin Airlines, Custom Helicopters, and Provincial Airlines.

In 2006, Perimeter acquired a 705 operating certification from Transport Canada, authorizing them to start flying larger Dash 8 aircraft.

2010 marked the 50th anniversary for Perimeter Aviation!

In 2012, Perimeter sadly had to make a business decision to close its flight school. This decision was rooted in the evolution of how flight training is delivered in the 21st century—the majority of training is now performed using flight simulators, and test flights are typically flown out of smaller airports that are less busy than the Winnipeg International Airport where Perimeter is based.

With more than 30 aircraft in it's fleet, and a certified Approved (Aircraft) Maintenance Organization (AMO), Perimeter now offers regularly scheduled passenger services, Aeromed air ambulance services, and cargo shipping to more than 22 communities in Manitoba and North Western Ontario; with the ability to provide custom chartered flights to any destination in North America.