A quarupole is a charge distribution (in case of electric quadrupole) with a higher order symmetry than a dipole. It is described mathematically by a tensor rather than a vector, so it's hard to visualize and very hard to draw out on a piece of paper. They say that two equal dipoles arranged in antiparallel fashion is the easiest description of a quadrupole, but I'd be lying if I said I could get that from the mathematical expression. I take the mathemeticians' word for it.
The quandrupole moment is magnitude of the effect. It is hard to measure exerimentally, which is probably why you don't see it very often.
There are spectroscopic implications of large quadrupole momen - most likely related to nonlinear optical effects - but honestly I couldn't tell you what they are off the top of my head. I'm more used to dealing with polarizabilities and hyperpolarizabilities, and how these are exactly related to the quadrupole moment is beyond my knowledge.