Daniel
If you fly into Philadelphia you can start your road trip with a real
Rodeo at The CowTown Rodeo in New Jersey. It started in 1929 and has been a
regular event since 1955, check their web site.
As you have seen in the responses everyone thinks their part of the
country is the best, again beauty is in the eye of the beholder. If you want
to see the country, small towns and meet the people, I still suggest flying
into an east coast city and taking an older US highway west taking your time
for the first 2 weeks save the third to make a dash to your departing city
if needed. This type of route will allow you to see the extremes in the
country side and meet the varied "locals" across the country.
I would suggest late August to mid September still warm most, families are
ending their vacations, the college kids are ending summer jobs and may be
looking to party some before heading back to school.
As to the New York to Miami route you would be traveling through the most
congested part of the country. Hitting mostly large cities which can be
bypassed but not easily, with little change in scenery.
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