I would have to believe that the Winton was brought in on either the Northwestern or the Milwaukee RR and Charles road on one of the passenger cars...then the car was unloaded and he drove it down Main Street.
The Winton Company recorded its first sale in March of 1898 for $1000 dollars and by years end, 22 Winton's were sold.
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The Winton Motor Carriage Company was a pioneer United States automobile
manufacturer based in Cleveland, Ohio. Winton was one of the first American companies to sell a motor car.
In 1896, Scottish immigrant Alexander Winton, owner of the Winton Bicycle
Company, turned from bicycle production to an experimental single-cylinder
automobile before starting his car company.
The company was incorporated on March 15, 1897. Its first automobiles were
built by hand. Each vehicle had painted sides, padded seats, a leather roof,
and gas lamps. B.F. Goodrich made the tires for Winton.
On March 24, 1898, Robert Allison of Port Carbon, Pennsylvania, became the first person to buy a Winton automobile
after seeing the first automobile advertisement in Scientific American. Later
that year the Winton Motor Carriage Company sold 21 more vehicles, including
one to James Ward Packard, who later founded the Packard automobile company
after Winton challenged a very dissatisfied Packard to do better.
1898 Winton ad