How do I know where and when to look?
For beginning observers, starting is sometimes the hardest thing to do. There really is no wrong or right way to look at the night sky, but knowing what you’re looking for helps. It is with great sadness that we, in the astronomical community, have learned that the most useful website, is no more. The cost was just to much to those who maintained the site. We will all miss it. Heavens Above is a good site for somewhat experienced observers. Astronomy Tools is a little more friendly to beginners.
Astrogoggles Carpe Caelum Observer’s Guide