Ok, I have my grandads pipe that was passed on to me years ago. I haven't tried it out in probably 15 years. What should I start with? Tobacco? Do I need filters for it? I have been smoking cigars for years and now have hankering to try out the pipe. Any input would be great.
Many say buy a package of drug store/over-the-counter (OTC) tobacco and light up. That's what I did (my dad owned a general store) but I don't recommend it.
I suggest you go to a decent tobacconist and, hopefully, the tobacconist will be able to recommend a few bulk blends for you to try. Bulk blends are usually quality tobacco in various types (English, Cavendish, Virginia, Aromatics, etc.) that you can buy small amounts of (they are sold by the ounce). Be sure to talk it up with him first so your tobacconist can get a feeling of what you might enjoy. Aromatics (like Lane's 1Q) are usually the first recommendation for n00bies, but see if you can try an ounce of a few types of tobaccos. Bulk blends usually sell for $2-$5 an ounce and many also come in tins.
Once you narrow down the types you like after sampling these (and maybe some others) you will, over time, find types of blends and brands you really enjoy.
If you live in East Bumf*ck (like me) and there isn't a tobacconist reasonably close to where you live, try calling one of the better on-line vendors toll-free (like Bobby at PipesandCigars.com, or Richard at 4noggins.com who will be happy to talk you through the process and provide you with some recommendations.
To get you started, here's a few bulk blends you might enjoy: Lane 1Q (aromatic), Mac Baren's 7 Seas Regular (aromatic), Peter Stokkebye Bulk Luxury Bullseye Flake (Virginia/Perique/Black Cavendish cut in coins, non-aromatic), Samuel Gawith Best Brown Flake (Virginia, non-aromatic), Hearth and Home Ambassador's Blend (English, non-aromatic).
Oh, and some important advice ... not as much of a problem in bulk tobaccos, but some pipe tobaccos arrive much too moist. If the tobacco clumps together when pinched, leave a pipe full out to dry a bit before packing your pipe. Don't pack tobacco too tightly in your bowl. Leave the finer "grains" of tobacco to the side and place those last in your bowl to make the tobacco easier to light. Get an inexpensive "pipe tool" (I have a Peterson knife/pick/tamper I paid $5 years ago) and a 2 packs (one each) of "regular" and "bristle" pipe cleaners -- clean you pipe after each smoke. Smoke (sip) your pipe slowly, very slowly -- important for all blends but especially so with Virginias.
The best "dimestore" tobaccos IMHO are the Captain Black White and the Gold. Borkham Riff isn't bad, either. Just knowing how "dimestores" work, do yourself a favor and throw you a small slice of an apple into the tobacco pouch to moisten it up a bit, because it's probably been on their shelf for a while.
I'm not a fan of pipe filters. Some filter pipes need them to get a decent draw, some are okay without without them, but like everything else, to each his own.