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Transportation
Shepherd used many methods of transportation

Shep loved to travel and often spoke about cars and driving down the Jersey Turnpike,  being out in his plane, or driving around New York on his motorcycle.

Note the photos, unless otherwise noted are symbolic of vehicles he owned and are not the actual ones.

Cars
Shep owned many cars, was the host of several car rally's in the Village and New Hope Pa, and was sponsered on the radio by several car manufacturers.
Motorcycles
According to one of the members of the Red Onion Jazz Band, which performed in "Look Charlie", Shep rode a "Cushman" You can see Shep on his Cushman on the first page of the "Look Charlie" program which Shel Silverstein drew. He is riding up the lower leg of the letter "K"
Planes
Shep owned a 1973 Grumman American AA-1A Yankee - FAA # N73JS and it is still registered under his name with the FAA
Bicycles

Shep claims to have owned a green Elgin bicycle as a kid. It was stolen when he went to the local A&P for bread and left it unattended out front.