I couldn't agree with t00rd more. Cheap department store scopes = about 60 minutes of frustration then you stuff the scope in a closet never to be seen again.
There's a lot of what-if's to picking a scope, but, a few questions to ask:
Relector/Refractor: Seems like most cheap dept store scopes are refractors (usually long skinny tubes), Refractors are great, but good ones can get expensive. 80mm seems to be a sweat spot I see more folks starting with Reflectors (these are long or short depending on design) and is what I am most familiar with. These are much about how much light you can catch, or how large the mirror is. 90,114, and 127mm short tubes are pretty plentiful and reasonably priced. Avoid the cheapest models though. I'm a fan of Dobsonians. They call these light buckets for a reason. The simple mechanics of a dob make it a good bang for your buck scope. There is another form of scope, catadioptroic, but these tend to be more than a beginner wants to spend.
Computerized: The computerized/go-to scopes are nice, but mechanics on say sub $300 scopes are shaky from what I have seen. Navigating to common objects isn't that difficult once you get the hang of it. You can get something like Stellarium http://www.stellarium.org/ to help navigate. There are apps for android and ios that will help too. If you go manual to start out with, you get a lot more bang for your buck. So, manual or power?
Size/weight: Are you going to have to carry it upstairs? Do you have somewhere to store a larger scope?
Something like this might be a good beginner scope, reasonably small and light: http://www.telescopes.com/telescopes/reflecting-telescopes/celes...
Since I can keep it in my garage on a dolly, I started with this a few years ago and have no reason to upgrade so far: http://www.telescopes.com/telescopes/dobsonian-telescopes/zhumel... It's a bit more, but the views I get are great.
This seems to be popular as well: http://www.telescopes.com/telescopes/refracting-telescopes/meade... also comes in larger sizes as well.
For brands, most brands make good and not so good. In general, avoid any model sold in a department store. Orion, Zhumell, and Meade make decent, affordable scopes.
Most scope packages come with enough eyepieces to get you started and keep you busy for a while. Avoid the urge to buy one of the $60-100 whiz bang eyepiece sets as these are often poor quality and may not work well with your scope. Put the money into a better quality scope and if decide to expand in the hobby, there's plenty of folks out there to help you pick ep's that work with what you have so you don't waste $$ on gear that doesn't help you.
As with most hobbies, each person is different, so this advice may only be worth the price you paid for it You can hang out for abit somewhere like cloudynights.com and get a wealth of info quickly. That would probably be the best way to get a feel for a good scope to start with.