Is the there an intended PCB layout for the MAX7219/MAX7221 I'm missing?
Looks like a tangle to me. Sometimes you just have to suck it up and route it regardless. If you really want a nice layout, slap it down and re-route it 4 or 5 times, trying to move components around to reoptimize. You'll eventually pick up enough tricks to do your optimal layout for this design.