Hi Matt
Where are you in Maryland ?...our home state for a while....Beltsville.
We moved to Oregon in 99 and have made the crossing many many many times.
I would strongly advise you to reconsider crossing the upper midwest at this time of year unless you only need to get somewhere.
There are so very many places you will miss.
There is so much potential of being tied to the Interstate and unending drudgery of endless truckstops....waking up at 14 degrees inside our van comes to mind.
Even crossing the southern tier of states is going to subject you to some high elevations and potential mighty rough weather.
Of course you may be seeking that sort of thing.
Travel safe.
DavidGraves
north Oregon coast