Sympatico.ca's online home to budget travellers. Europe and the England are very popular spots for first time backpackers. Those with a little more time and money can take a look at Australia or Asian countries later on in your trip. Backpacking Europe has a good basic guide to help you make your decision. It will give you tips on what to wear as well.
Checklists are very helpful when planning a trip.
The Backpacker Network gives you printable checklists for equipment and even for an international phone list. Backpacking Europe offers a good estimate of how much it will cost for a few months in Europe. You might also want to browse through Sympatico's Travelocity Best Fare Finder to see how much your flight might cost. Eric's Backpacking Page gives you a detailed break down of how much you'll have to spend and on what. You may want to consider working abroad to finance your travels.