Found this one on the SUNY Stony Brook Math Problem of the Month archives.
A county has <m>n > 4</m> cities. Is it possible to connect some pairs of cities by one-way roads so that one can travel from every city to every other city using only one or two roads? If so, how? Note that for every pair of cities A and B, only one road connecting A with B is allowed; this road leads from A to B or from B to A, but not both ways.