I realize I'm a little late to the party...
I've smoked a pipe for 23 years so I've formed some opinions, some are contrary to those already stated. I'm not looking for an argument, just stating a different view.
Cobs can be a cheap, satisfying smoke but I think they generally have cheap stems and impart an odd flavor that might put off a newbie.
I'm also not very partial to Dr. Grabows. They're generally of lesser quality and are often sealed with an airtight finish that prevents them from "breathing". You get what you pay for.
I think starting with a Peterson is a good idea. Also check out Bjarne, Brebbia, Stanwell, and Savinelli. All make excellent entry-level pipes.
As for tobacco, I disagree with whomever said that Burley has 'good flavor' or something to that effect. It's essentially flavorless (virtually no natural sugars) and high in nicotine. It's the primary ingredient in U.S. cigarette (along with shredded paper and lots and lots of chemicals).
On the other end of the spectrum is Virgina tobacco; high in natural sugar, which means lots of natural flavor. But be careful because sugar burns HOT, so take your time smoking Virginas. It also has little to no nicotine. I had a lengthy discussion about this with Per Jensen of Mac Baren tobacco a few years ago, and he assured me that straight Virginia tobacco has practically no nicotine and thus not addictive.
Armomatics is a catch-all term for Burley or Virngina (or a combination of each) with flavorings added either during the mix or sprayed on after. These flavorings are usually sugar-based, so they will burn even hotter. Most pipe smokers get their start smoking aromatics.
Personally I don't care for Carter Hall, Sir Walter Raleigh, Captain Black or other drug store varieties. They generally use low quality tobacco and load it up with sugar, humectants and other chemicals. I think the two best brands of tobacco produced in the U.S. are McClellands and Cornell & Diehl. They both use the highest quality tobaccos and have enough varieties that you should find something you like. I think Mac Baren and Stokkebye both make fine tobaccos as well.
So find a good tobacconist and tell him what you're looking for. He should set you up with enough different samples that you can make up your mind about what you like and what you don't.
Just take your time, pay attention to what YOU like and it doesn't matter what anyone else thinks.
Especially me.