On the Road Part 1, Chapter 2
In July 1947, Sal leaves New York with fifty dollars in veteran benefits. A friend, Remi Boncoeur, has asked him to take a round-the-world cruise with him. Remi, a crazy man Sal knew from prep school who was living in California with a woman named Lee Ann, expected Sal to arrive in ten days. Sal's aunt approved of him leaving and took care of his manuscript. Sal has been looking at U.S. maps for months in anticipation, and decides to take U.S. Rt. 6 all the way for scenic reasons.
"If you drop a rose in the Hudson River at its mysterious source in the Adirondacks, think of all the places it journeys by as it goes out to sea forever- think of that wonderful Hudson Valley. I started hitching up the thing. Five scattered rides took me to the desired Bear Mountain Bridge, where Route 6 arched in from New England." Part 1, Chapter 2, pg. 12
At this point, there is no traffic and it begins to rain; Sal is forty miles north of New York City. He finds shelter under an abandoned filling station. A car drives up and offers him a ride back to New York City, advising him that he is too far north and would have more luck going to Chicago through Pittsburgh. Sal reluctantly agrees and ends up spending a good portion of his money on a bus ticket from New York to Chicago.