Several pioneering cross-Canada automobile journeys shaped the dream of a national highway and helped define Canada’s identity through mobility. These tours — some quests for medals, route retracings and reenactments — span over a century and offer insight into changing technologies, ambitions, and road conditions.

1912 - Jack Haney and Thomas Wilby 

The earliest was the 1912 expedition by Thomas Wilby and Jack Haney in a REO car. It was the first serious successful attempt to drive from Halifax to Victoria, although they did not qualify for the Todd Medal because their 1912 journey was not completed entirely on Canadian roads.

1920 - Percy Gomery

In 1920, Percy Gomery published A Motor Scamper ’Cross Canada, recounting his own car trip from Montreal to Vancouver, capturing the sense of novelty and human curiosity about Canada’s vast, disconnected roadways. He dedicated his book to Dr. Doolittle, the "Grandfather of the Canadian Highway."

1920 - T.A. Langstaff

That same year, T.A. Langstaff led a REO Six cross-country tour to promote the car’s rugged capabilities, a kind of publicity event meant to showcase mechanical reliability more than a continuous road. 

Images courtesy of the City of Vancouver Archives.

1922 - The Yellowheads

On June 17, 1922, Charles Neiymer and Frank Silverthorne set out in an Overland Four to conquer the first automobile crossing of the Yellowhead Pass, backed by Edmonton's Lines Motors.

George Gordon and J. Sims followed in their Model T Ford, sponsored by the Automobile Association of Canada. Both expeditions reached Victoria, apparently earning medals for their trailblazing journeys along a path later dubbed the "tote road."

Source: https://www.canadianrockies.net/jasper/yellowhd.html

1924 - Austin F. Bement and E. S. Evans

Austin F. Bement and E. S. Evans, associated with the Lincoln Highway Association, took a Packard across western Canada from Winnipeg. The Packard Motor Car Foundation’s account describes their use of railway tracks, with railway permission, where roads were unavailable.

An attempt to use special flanged wheels proved unsatisfactory, and they continued on ordinary rubber tires. They received the gold medal for completing the western crossing under the car’s own power. Packard Motor Car Foundation, “Riding the Rails in Canada in a Packard”.

1925 - Dr. Perry E. Doolittle, Ed Flickenger, and Ford Executives

Dr. Perry E. Doolittle, a Toronto surgeon and avid cyclist, founded the Canadian Automobile Association (CAA) in 1903 with a bold vision: to connect communities across Canada through better roads.

Known as the "Father of Canadian Good Roads," and an early adopter of the automobile, he used it for medical house calls and tirelessly advocated for safe, uniform road laws.

Key achievements include:

• 1913: Led CAA to install Ontario’s first road signs.
• 1919: Helped push the Canada Highways Act, securing federal support for interprovincial roads.
• Fought for standard traffic rules across provinces—at the time, some only allowed cars on specific days.
• 1923–25: Promoted and organized cross-country road trips, including a famous 1925 journey from Halifax to Vancouver in a Ford Model T, which tested rail-mounted wheels for unbuilt segments of road. They would use flanged wheels so they could travel on railway tracks.

Source: https://caamagazine.com/on/good/caa-founder-dr-doolittle

According to Mark Richardson, Dr. Perry Doolittle did not drive across Canada in 1925 the entire way. He designed the route and briefly joined the publicity tour in Quebec to drive across the railroad bridge and drove near Dryden but he mostly traveled by train.

The myth that Doolittle completed the journey apparently began with a 1973 Ford PR campaign and was never fact-checked. Ed Flickenger, a filmmaker and photographer with Ford, piloted the entire journey. The driving was handled by a rotating team of Ford regional executives along the route. 

A brochure of the Ford company in 1997 (on file with the filmmakers of "Chasing the Trans-Canadian Dream") confirms that Flickenger was one of the drivers but does not mention Ford's regional executives driving the car.

1928 - J. Graham Oates

On July 21, 1928, J. Graham Oates dipped the rear wheel of his motorcycle, “Toby,” into the Atlantic Ocean at Halifax. Sixty-three days later, on September 22, he baptized the machine in the Pacific at Vancouver’s English Bay.

It was the first successful motorized crossing of Canada on rubber tires without switching to flanged wheels for travel on railway tracks. He drove with rubber tires for some 900 miles of riding between railway ties!

The journey spanned 4,027 miles over 21 riding days, a grueling ordeal marked by breakdowns, and a solitary test of endurance, ingenuity, and nerve.

Source: https://d945.canadianmotorcyclehalloffame.ca/inductees/2009/j-graham-oates

1946 - Brigadier Alex Macfarlane

The Todd Medal was finally awarded in 1946 to Brigadier Alex Macfarlane and navigator Ken MacGillivray, who drove 4,743 miles a new Chevrolet Sedan from Louisbourg to Victoria in just nine days.

Their trip was the first verified crossing entirely on Canadian roads, thanks in part to wartime road construction in northern Ontario. The Chevrolet used was a stock 1946 model powered with a standard six-cylinder valve-in-head engine. 

The 1960 CBC Radio Tour

In 1960, with the Trans-Canada Highway still under construction, CBC radio launched a coast-to-coast road trip titled Trans-Canada by Car. The 7,821 km journey was undertaken by CBC radio hosts Ron Hunka and Doug Brophy, accompanied by technician Ken Frost. They left St. John’s, Newfoundland on June 28, 1960, aiming to reach Victoria, B.C. by July 28, 1960.

Key features of the trip included:

• Daily radio segments broadcast from 23 towns and cities across the country.
• A Chevrolet Impala specially modified with heavy-duty shocks and a large battery to power a Magnecorder tape-editing machine.
• The symbolic carrying of a flask of Atlantic Ocean water and a message from the mayor of St. John’s to Victoria.

Challenges they faced:

• Time zone changes disrupted their schedule daily.
• Montreal’s rush hour nearly made them miss a live segment.
• Rogers Pass in B.C. was incomplete, forcing them to split up: Hunka crossed with a Department of Transport engineer in a Jeep while Brophy and Frost detoured in the Chevy via the treacherous Big Bend Highway.

The car was sponsored by General Motors, and product mentions were made during segments (advertising on CBC Radio was phased out in 1975).

https://cbc.radio-canada.ca/en/your-public-broadcaster/blog/Trans-Canada-on-the-radio

1963 - Edward McCourt

In 1963, Edward McCourt drove the full Trans-Canada Highway shortly after its official completion and published The Road Across Canada, a reflective and literary account of the changing country seen through the windshield.

1997 - Lorne & Irene Findlay, Peter Findlay and John Nicol

In 1997, Lorne Findlay recreated Wilby and Haney’s 1912 drive in a restored REO, following their original route to commemorate its 85th anniversary. Peter Findlay and John Nicol accompanied him.

2012 - Mark Richardson

In 2012, journalist Mark Richardson marked the 100th anniversary of Wilby’s trip and the 50th anniversary of the Trans-Canada Highway by driving coast-to-coast in a modern Camaro. He carried the original Todd Medal, a 1925 CAA radiator badge, and even a horseshoe from Wilby’s car.