Let's start with the fact that you don't actually need a telescope to enjoy astronomy. There's a lot to see with just your eyes, and even more with a simple pair of binoculars. Experienced amateur astronomers with many thousands of dollars worth of equipment almost always have binoculars as well - they are convenient, economical, and can be used for other hobbies like bird-watching.
Here's a few good guides for getting started with naked-eye or binocular astronomy:
Some of our members recommend this as a fun book for learning the the constellations.
The Stars: A New Way to See Them by H. A. Rey
Both of these are good beginner guides and both help answer the question of what to look at; either with binoculars or with a small telescope.
Turn Left at Orion: Hundreds of Night Sky Objects to See in a Home Telescope - and How to Find Them by Guy Consolmagno and Dan M. Davis
NightWatch: A Practical Guide to Viewing the Universe by Terence Dickinson
If you are thinking of getting a telescope for yourself or as a gift for someone else, there's a lot of free advice on the Web. Here are some pages that we've found to be helpful: