Shane, there is no old town area in San Mateo so to speak. However there is nice down town (between 2nd and 4th Ave and B and El Camino Real) and great area to be in the evening is "B Street Theatre District (a part closer to B Street). The place is very vibrant. Plenty of good entertainment, for example a wine festival last weekend. Great restaurants (check Lure!). A simply nice place to hang out. And of course movie theatres. Click on the link below to find out more interesting trivia about San Mateo. The good news is that you can have a great house near buy (either in San Mateo or Hillsborough and walk to the down town area in less than 10 minutes!