Part 1 - Purchase Options

There are three main options to explore:

1. Buy a new (or old new stock) bike from a local dealer
2. Buy a used bike through eBay, Craigslist, Uncle Henry's, or something similar
3. Buy a new bike through the internet

Buy a new (or old new stock) bike from a local dealer
This will cost the most money, but is the typical way to make a purchase.  Besides brand new (current year models), see if the shop has any "old new stock".  These are still new but may be last year's model saving you some money.  What ever option you choose, you want to establish a good relationship with a bike shop.  They will help maintain and fix your bike when needed.  If you choose options 2 or 3, they might be a little less helpful (at least initially).  Go to the local shops to see and test bikes and get a good idea of the size you need.  Not all manufacturers size the same.  Fit/size is the most critical thing ... you can have the fanciest bike in town, but if doesn't fit you, you're hosed. I am not familiar with any shops in Bangor. In the Winthrop/August area there are four primary choices:

1. Mathieus Cycle (Oakland) - probably the best local shop. Pretty good selection and carries several brands including Trek, Specialized, Scott, and Cannondale. Take a look at the models on the manufacturer web sites to start to get an idea of what the options are.
2. LL Bean (Freeport) - the main store has a nice bike shop and carries Felt as well as some other brands.
3. Tom's Bike Boutique - this is the guy that sponsored Seth.  He is primarily a mechanic (and a good one).  He would be a great guy to chat with and use as your primary mechanic.  He doesn't seem to sell a lot of road bikes, but may be able to.  If you go with options 2 or 3 above, he can help assemble and then maintain.
4.  Auclair Cycle (Augusta) - nice guy and knows the family.  That said, he does not carry the best bikes and does not cater to higher end stuff.

Buy a used bike through eBay, Craigslist, Uncle Henry's, or something similar
You can get a lot more bike for your money (better frame, components, etc.) buying a used bike, but it will be a used bike.  That means a few scrapes potentially and most important, you need to really check out the bike to make sure it fits and is in good shape.  I bought my winter bike on eBay, so it can work.  Check out eBay, Craigslist, Uncle Henry's and see what you find. Again, you can get a bike that originally sold for a lot more money this way.

Buy a new bike through the internet
Some manufacturers will not let their bikes be sold over the web, but some do.  If you find a bike you like locally, see if you can find it online cheaper.  The local shop may match the price or come down some.  There are a few online dealers worth looking at.  You get a lot for your money this way, but will need a local shop to help assemble it (not from scratch).  Of particular note is Bikes Direct and Performance. Bikes Direct sells Motobecane and you get a lot for your money.  The brand used to be a big European player.  Performance has their own brand, and again you get a lot for your money.  They need finally assembly and some purists shy away from the brands, but good bang for your buck.