score:5
You can find daily weather maps of the lower 48 at http://www.hpc.ncep.noaa.gov/dailywxmap/ since 2003; there are historical maps from 1871-2003 available at http://docs.lib.noaa.gov/rescue/dwm/data_rescue_daily_weather_maps.html but you'll need to download an additional plugin.
The article at http://en.wikipedia.org/wiki/Climate_of_the_United_States includes a basic climate map and links to descriptions of the seasonal characteristics of the "humid continental" and "humid subtropical" climate types.
Between http://www.worldclimate.com/ and http://www.weatherbase.com/ , you can find average weather for different stations for different months from around the world. I'd start with WeatherBase, as its data is more useful in my opinion, e.g. I prefer a temperature range to a mean temperature. On the other hand, WorldClimate includes more stations, and you don't need to convert if you don't know Fahrenheit.
For planning a road trip, I would not think weather would be your primary concern; it's hard to find a rental car without air conditioning, and in the north or in the mountains where you are likely to see snow in winter, the road crews are very good about keeping the highways and arteries clear (ice and snow are most dangerous where drivers are unaccustomed to it, like D.C. or Dallas). At any time of year there is the risk of a thunderstorm, tropical storm, and/or blizzard, but they are not predictable.
Pay closer attention to traffic patterns in and out of cities (e.g. don't leave for the Hamptons from New York City at 5pm on Friday), gasoline prices, and phenomena like the "driving season" between the last Monday in May (Memorial Day holiday) and the first Monday in September (Labor Day holiday) when traffic and fuel prices are higher.