I've been smoking pipes and cigars for more than 40 years. In fact, there were still real Cubans cigars "under the counter" in tobacco shops while I was in college.
We joke about gas station and drug store cigars, so why buy pipes or pipe tobaccos from such vendors? Sure, many will say "start with Prince Albert or Carter Hall, etc. (usually called "old codger" blends) and a cheap briar off a cardboard display, which is actually the way I started, but that's not the way I'd advise anyone interested in smoking a pipe.
Get a good Missouri Meerschaum (avoid the less expensive MMs and no-name look-alikes, one costs about $8) -- you can usually find a good MM your local B&M -- most B&Ms sell pipe tobacco as well as cigars and many sell a variety of pipes as well.
You can pick up a ton of help from a knowledgeable tobacconist. Most sell a variety of "bulk blends," which are sold by the ounce, so once you learn the differences from you tobacconist, you can decide which variety of their bulk blends to try -- one ounce (about $2-$4) at a time. Most pipe n00bs start with a good aromatic, like Lane's "1Q," which is a bulk blend available at many, if not most decent tobacco shops. I smoke Virginias, Virginia and Perique (VA/Pers) and some English/Balkans.
Like cigars, your investments in time and effort learning about pipes, pipe tobacco and pipe smoking (all of which are at least as complicated as cigars if not more so) will repay many times over in satisfaction and enjoyment.
