[This is post a cross-post from G+, since I hope it will be of use to others in the future.]
Figuring out wilderness map scales is tricky -- particularly so for hexcrawls. In fiction, characters move at the speed of plot, but in RPGs and wargaming, better precision is needed.
So, use the real world to help you visualize distances that you are already familiar with. That may help you understand how your wilderness map should look.
PROTIP: Google maps is a great tool for this exercise.
Recall that wilderness hexes in B/X "default" to 24 miles. That's because it aligns with PC movement rates well. An unencumbered PC travels one hex per day.
But a map scaled out to 24 mile hexes loses a lot of detail.
A more useful hex size, at least for hex crawling, is 6 mile hexes.
Above is a map of my beloved Bay State. The google map scale here is 5 miles per inch (there is no 6 mile zoom option). Each square is an inch (I could not get any hex grip plugins to work on gimp tonight).
That gives us roughly a 4 square per day movement rate.
As the crow flies, I live about 5 squares away from Boston. Were I a PC, it would take me some part of two days to get to Beantown, if I met with no encounters. A traveler from Boston would need a full two days to get to Worcester (not shown, but east of the map). Hyannis (a town roughly in the middle of Cape Cod) is about 3 days travel. New York City (43 squares)? About 11 days travel (actually 12, since the rules say that PCs travel for 6 days, but must rest on the 7th).
Try this exercise with a location familiar to you. I hope this makes sense and helps make your wilderness maps even awesomer, although I already see a lot of sweet, sweet maps in the OSR community.