Where you will use your phone will determine whether or not you get a long-distance plan. Some plans focus on giving you a good deal if you stay in a certain area and only make local calls. Other plans allow more leeway for travel and long-distance calls, by giving you a less expensive rate for long distance, while ignoring where your calls are made from and who you are calling.
"Roaming" is when you make a call outside your Home Service Area (where you set up your account). Usually, an additional charge is levied for this service. Fewer and fewer companies are imposing roaming charges, so it may be a good idea to check the policy of the plan you are interested in to see how it is addressed.
When you get a cell phone, you're going to have to contact a local service provider, because it's their airwaves you'll be using. To find a provider nearest to you (and to find out about every single deal they offer), try a site like LetsTalk.com (see Resources). Type in your zip code, and it'll direct you to your nearest providers, as well as tell you about each one.
In addition to determining where you will use the phone, you will need to consider when your calls will be made, and if you want web access.