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Road Trip For Two

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My boyfriend and I fantasize about going on a road trip from Oregon to New York, but we really have no idea where to start! We also want to go down to Kentucky and up to Michigan to visit my family! I imagine this would be at least two weeks, maybe even three!
The idea is to go across the country, but we have no idea where to stop!
We are huge nerds, but not so much into the national monument thing.
Do you have any suggestions for states/places to stop?
Where should we start with costs? This will be our first real trip and we just don't even know where to start!

Thank you!

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