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Taking Flight

This story was researched and written by Emerging Historian Shannon Buskermolen (2025) and made possible by the generous support of our Tours Program Presenting Sponsor, TD Bank Group through the TD Ready Commitment, and Toronto Port Authority.

Last updated: November 24, 2025

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Crash Landing on Toronto’s Waterfront

Toronto’s waterfront was an important feature from the early onset of aviation in Canada.

Aviation was taking off during the early 20th century, and Toronto was no exception to the action. While largely considered for its role as a mode of transportation today, aviation at the time was considered to be a sport for the brave few who dared to conquer the air. From sport and leisure to airmail and passenger transportation, Toronto, especially its waterfront, was a key location in the early history and development of aviation activity in Canada. 

In the early days of aviation, aviators (or “birdmen”) would showcase their aircraft and flying skills, often seeking to win prize money, break records, and test innovations in the sport at aviation meets or flying exhibitions. The first public exhibition of flying in Canada, if not North America, took place in Toronto at Scarboro Beach Park on September 7, 1909. It was there that aviator Charles Willard and his “Golden Bird” flew Toronto’s first flight. 

Unfortunately, Willard’s first attempt resulted in him crashing into the water before he could properly take off. Local papers reported on his “rather [disastrous]” attempt with headings like “Airship Went Up and Airship Came Down.” However, this did not stop him from trying again. His final attempt, fitted with cushions beneath the aircraft’s frame should he fall into the lake, was a success as he took flight over Lake Ontario for five minutes. The feat was met with sheer excitement from spectators who gave Willard “[q]uite a cheer” when he landed again. 

Not long after, Toronto experienced another impressive flight, this time the first flight to fly right over the city itself. In July of 1910, Count Jacques de Lesseps flew his Le Scarabee from an aviation meet at Trethewey Farms in North York over the city to Lake Ontario, over the Toronto Islands, and back. These early exhibitions of this new technology were just the beginning of the Toronto waterfront’s continued presence in, and contribution to, aviation history.

Sepia photograph of people standing around an early-style airplane in an open field. The plane's wings are blocking the people standing around it, so only their legs are in the image.

Toronto Islands Take Flight

The Toronto Islands witnessed greater spectacles of aviation as technology advanced.

Charles Willard once again found himself making aviation history in Toronto in 1911, alongside John McCurdy, the first Canadian aviator. The pair flew the incredible distance of 35 miles from Hamilton to Toronto. Willard flew the distance along the shoreline, landing at the Exhibition Grounds, while McCurdy flew over the lake and landed on Fishermans Island, once part of the Toronto Islands. 

Boats and trains could not compete with the speed of the airplanes. The flight took Willard 43 minutes to complete, and McCurdy 36 minutes. It was a true testament to the abilities of the airplane and the future possibilities of air travel. Despite the historic achievement, local papers noted the enthusiasm of the crowd was less than the year prior. Reporters saw this as a compliment and an indicator that aviation was becoming common, soon to be regarded in the same manner as an automobile.

Even still, the sport of aviation was a spectacle enjoyed by many for years to come and was a highlight of the Canadian National Exhibition in its early years. The Toronto Islands were also the location of such a spectacle with a race between the relatively innovative “flying boat” and a hydroplane (motor boat) in 1914. The Sunfish flying boat won what was considered an exciting race against W.H. Gooderham’s speedy hydroplane. Experimentation with and advancement of the flying boat, or seaplanes, was essential to the Toronto Islands as a site of aviation, and vice versa, due to its unique location on the waterfront. 

The same year, the Sunfish, piloted by Macauly, flew Toronto Star reporter Lou E. Marsh on a flight between Toronto and Hamilton. The flight aimed to beat the previous benchmark for flight time between the two cities set by McCurdy in 1911. Despite Marsh’s fears of crashing, the flight was practically seamless and succeeded in its goal, beating the record by 3 minutes. The flight demonstrated the advancement in aircraft capability over the past three years. More than just technological capability and spectacle, the flight also marked the time a passenger had travelled by air between Toronto and Hamilton.

Black and white image of two men relaxing on a "flying boat" on the lake. The propeller and double wings are in the foreground of the image

Training for Glory

The British Empire’s entry into the World War I, also known as the Great War, led to increased training and aviation activity on the waterfront.

In addition to these few private inter-city flights, the Toronto Islands saw the shift from aviation as a sport and spectacle to the use of aviation for more practical purposes in another way as well — namely, military training. McCurdy was an important figure in the advancement of aviation and a strong supporter of a national aviation corps. Eventually, in April of 1915, a Curtiss Aeroplanes and Motors Ltd factory opened and began operations in Toronto at 20 Strachan Avenue near the Exhibition Grounds. The factory assembled aircraft such as the Curtiss Model “F” flying boat and others for the war effort.

The horrors of war were not fully known yet to those on the Home Front. Enlistment was still seen as a patriotic duty to the Homeland (Britain) and an opportunity for adventure. Being a pilot was seen as a glorious role akin to cavalry. As such, Curtiss Flying School opened on the Toronto Islands at Hanlan’s Point to train individuals before they were sent to fly overseas. A wooden hangar was built on the beach with a ramp into the water to allow trainees to learn to fly and operate flying boats.

After the war, there was an abundance of aircraft and trained pilots. Aviators found themselves in possession of personal aircraft and greater skill. While airshows at the CNE were still taking place, it took “more than races and steep turns to keep spectators coming.” It was becoming increasingly difficult to make a living on exhibitions and spectacle alone. As a result, many aviators began to use their skills for more practical and commercial purposes.

An ad from a 1930s Toronto Star newspaper detailing air services provided in Toronto, including seaplane flights from Toronto Air Harbor for five dollars.

Airmail and Charters, Oh My!

Commercial and practical uses of aviation on the waterfront increased following the Great War.

Billy Bishop and William Baker were two of Canada’s top flying aces during the Great War. Upon their return to Toronto, the pair acquired three war-surplus seaplanes, Curtiss HS SL flying boats, that were designed to hold three people. Using these aircraft, Bishop and Barker opened Toronto’s first commercial aviation company, Bishop-Barker Aeroplane Ltd, in 1919. They provided air charter services from Toronto Harbour to cottage country in the Muskokas.

While their company only operated for a few years before bankruptcy, their activities on the waterfront, along with other similar operations, were important to the opening up of Ontario’s North. Seaplanes were an integral transportation method in northern regions, which previously relied on boats. The summer months were especially busy with tourists seeking transportation to the Muskokas for their getaway from the city. It further highlighted the waterfront as a key feature of Toronto’s commercial aviation opportunities.

Years later, in 1929, the Toronto Harbour Commission opened Toronto Air Harbour at the foot of Scott Street. It was a true accomplishment in the development of aviation in the city as “Toronto’s first civil air harbour and commercial seaplane base.” On July 15, 1929, the air harbour experienced its first landing. The flight was Canada’s first airmail flight between Buffalo and Toronto, carrying 14,000 letters across the border.

Offering scheduled seaplane services, Toronto Air Harbour was the only registered seaplane base in Toronto, and one of the few licensed air harbours in the world, where passengers landed within four minutes’ distance to the downtown core. The location of the Toronto Air Harbour on Toronto’s waterfront was integral to the future development and decision-making for an official city airport. Together with previous charter flights and commercial aviation activities, operations at the seaplane base were the beginning of Toronto’s entry into the “aviation age.”

Black and white aerial image depicting a vertical and a horizontal airport runway on an island. The mainland is on the left, separated by a narrow gap of water. A baseball diamond and city buildings fill the mainland.

Welcome to the “Aviation Age

The creation of a city airport on the Toronto Islands and in Malton would transform Toronto’s air travel industry.

It was decided that none of the existing smaller airfields, with grass landing strips and wooden barns for hangars, would be suitable for the fast-growing cross-country and international passenger service. Not wanting to delay any further, an advisory committee was created to help choose the location of the city’s airport. The top two contenders were Malton Airport (now Toronto Pearson International Airport) and an island airport on the western edge of the Toronto Islands at Hanlan’s Point.

Similar to Toronto Air Harbour, Toronto Island was believed to be a prime location for Toronto’s new airport due to its close proximity to the new hotel (Royal York) and railway station (Union). The importance of the waterfront, as had been demonstrated throughout its history of aviation, was not forgotten. Experts and officials stressed the need for a seaplane base in Toronto to accommodate transatlantic flights and Northern Ontario air development, specifically in relation to tourism and mining. However, Malton was preferred by some due to its existing infrastructure and larger space to easily accommodate expansions as air travel increased.

In the end, both airports were approved. The island airport was to act as the primary airport to allow for seaplanes in addition to landplanes and to provide passengers with quick access to the downtown core. Malton would be an auxiliary airport in the case of bad weather on the island and for other aviation needs.

Construction of the island airport began in 1937 and required the relocation of existing cottages and extensive lakefill to expand the island to build runways that could accommodate passenger planes. An administration building, known as Terminal A, was also built on the island’s edge of the Western Gap. Terminal A was an important structure in distinguishing the airport from the smaller airfields of previous years. It would serve many roles for the airport, including airmail facilitation, passenger processing, customs and immigration, baggage handling, administration, and air traffic control.

On September 8, 1939, Tommy Dorsey and his swing band arrived on the first commercial flight at the island airport. The airport received rave reviews for its splendid facilities, recognizing it as a major feat in aviation engineering on the continent. With the historic landing at the new Toronto Island Airport, “Toronto had finally entered the ‘aviation age.’ “

Continued Legacy

The legacy of Toronto’s waterfront as a key feature in aviation has continued to this day.

Although the island airport did not emerge as Toronto’s main airport as originally intended (largely due to poor weather conditions and its limited space), it still developed into a world-class airport over the decades. The island airport, now Billy Bishop Toronto City Airport, is the ninth busiest airport in Canada, and the fifth busiest airport with flights to the United States. It offers service to more than 20 cities in Canada and the U.S. with connection opportunities to over 100 international destinations. In addition to scheduled passenger air travel, Billy Bishop maintains many of its former aviation operations, including a seaplane base, with hangars housing aircraft for flight schools and charter flights.

The Terminal A building, now moved south of the runway, is also a reminder of the Toronto waterfront’s integral role in transforming Toronto’s air travel. The architecture of the building is typical of terminal buildings from before the jet age. It is one of the oldest terminal buildings in Canada, dating from the formative years of scheduled passenger air travel, and one of the few remaining in the world.

Reporters in 1910 had predicted that the airplane would become as common as the automobile and that soon the average person would take to the skies themselves. The waterfront and Toronto Islands were a key site to many of these changes, contributing to the shift from aviation as a sport for the few to a vital transportation method for millions of people.

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Further Reading

Bateman, Chris. “That time a fish-shaped plane made Toronto history.” blogTO. Article published June 21, 2014. 

Billy Bishop Toronto City Airport. “History of the Airport.” Billy Bishop Airport.

Canadian Aviation Museum. “This Month in Canadian Aviation History.”

Downsview Aerospace Innovation & Research. “Canada’s First Exhibition Flight – September 1909.” DAIRhub. Article published July 13, 2023.

McCaffery, Dan. Billy Bishop: Top Canadian Flying Ace. Halifax: Formac Publishing Company, 2017.

Taylor, Bill. “Once Upon A City: The Turbulent History of Toronto’s Island Airport.” Toronto Star, May 3, 2024.