Describe a trip that you can imagine taking from here to New York City, while stopping at five or more specific location

[answerhappygod]

Describe a trip that you can imagine taking from here to
New York City, while stopping at five or more specific locations
along the way. Describe each of these destinations in detail and
why you would go there. Use the Internet to research your trip.
Travel by train and/or by car. Assume that you have plenty of time.
You can use Google Maps or something similar for routing advice. Do
not pick just coastal locations. I want to see some stops in the
Midwest and South. Use this opportunity to educate yourself about
the interior of America.