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I came across this story about the first transcontinental motorcycle trip. 1903
This had to be a real adventure. Bad roads, no parts, even finding gas was a problem. 3800 miles in 50 days.
May 16, 1903 - The First Transcontinental Motorcycle Trip

On this day in engineering history, George Adams Wyman left San Francisco on the first transcontinental motorcycle trip, a 3800-mile journey which ended in New York City some 50 days later. Wyman's ride aboard a 1.25-hp, 90cc. 120-mpg motorcycle was also the first transcontinental trip on any motorized vehicle. A native of Oakland, California, George Wyman was a champion bicyclist who had once pedaled his way around the perimeter of Australia. After returning to the Bay Area in 1902, however, he discovered motorized bikes (as motorcycles were sometimes called) and took a summertime trip to the Sierra Nevadas, where he decided upon a future transcontinental trek.
From the Golden Gate to the Windy City
On May 16, 1903, George Wyman mounted his 90-lb. motorcycle and left San Francisco in a three-piece wool suit with a tie and cap. Because passable roads were rare, he rode along railroad ties after he left the city. In the Sierra Nevadas, Wyman's bike foundered in deep snow, forcing the uneasy rider to pass through wooden train-tunnels that clung to the mountainside. Sometimes, the former bicyclist helped power his 1.25-hp motorbike by pedaling up steep grades. Sand, mud, and livestock were also common impediments. Although a shepherd in Nevada cursed Wyman and his noisy motorbike, a rancher in Wyoming helpfully hitched-up a team of horses to pull the sunken vehicle from thick, cold mud.
From the Windy City to the Big Apple
George Wyman performed all of his own maintenance, often using materials found along the roadside to make repairs. As he neared Chicago, however, his engine broke a crank. For nearly a week, Wyman waited in the Windy City for replacement parts to arrive. By the end of June, he was on his way again. Summer weather had arrived, and finding gasoline and oil became easier as Wyman entered more populous parts of the country. In Buffalo, New York, an automobile manufacturer offered to service Wyman's motorcycle and loan him a car to take a tour of the city. Upstate New York was not without trials, however. Once, Wyman had to stop five times in one mile to make repairs. Frustrated, he nearly abandoned his quest. By the time the California biker reached Albany, New York, his vehicle's motor was beyond repair.
Fortunately, the 25-year old adventure-seeker was in good physical condition. George Adams Wyman pedaled the final 150 miles to New York City, arriving in the Big Apple on July 6, 1903. After attending the first meeting of the Federation of American Motorcyclists (FAM), he returned to California aboard a train.
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Could you imagine if you had to make that ride on a Kingpin?!?!...sorry, couldn't help myself.
That is a really cool story. the mountain passes and off road portions would have been very interesting.
 

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The family story goes:

My Dad's father rode a Harley in Philadelphia in the 1900's.
He was called "The Flying Dutchman" (Immigrant from Austria).
It was told that for a money bet he would let air out of the tires & jump it up on a rail road track & ride the train trestle across the river to NJ & back.

I have pics of him & the bike & it is the old pedal model with a carbide head light. 1915 or so????

My grand ma used to tell about them riding the bike from Philly to Atlantic city when it was a dirt road.
Hit a bump & bounced her off the back & she waited for a 1/2 hour for him to realize she wasn't on back anymore.
 
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