 It truly is a great time to be a pipe smoker! There has been a resurgence in recent years of the tobacco blending art, and many new blends have hit the scene. Not only that, but many blends that haven't been produced in years, sometimes decades, are making a return to the scene! Gone are the days of choosing one blend and smoking it for 80 years; as with pipes, there are literally HUNDREDS of choices. I always recommend trying at least one from each of the following blend types to help you figure out what types of tobaccos you like. Some of my recommendations are a bit muddled because of the inclusion of other tobacco types, but I feel these blends are good starting points. Aromatics This is the blend type that I think is most associated with pipe smoking, and thoughts of grandpa. I would recommend starting with a simple flavoring, like Vanilla. You can branch out into Chocolates, Rums, Whiskeys, Cherries, and other Fruit Essences from there.
Natural Virginias From the lighter grassy/hay-like Virginias, to the medium-bodied bread notes, to the heavily aged plum-like or vinegary Dark Virginias, there's a wide spectrum of flavors here, but all share the most notable sweetness of the Virginia leaf, which has the most natural sugar content of any type of tobacco. Virginia based blends also seem to age the best in general, and are often found in flake form.
Natural Burleys Often described as having a nutty or earthy taste, Burley blends can put some people off because of the “harsh” room note of the heavier blends, but can be some of the easiest to smoke. Some either like or dislike Burley because of the similarities to cigarette tobacco, since most cigarettes are made from burley. However, you don't get (or miss) that acrid burning paper note that comes from cigarettes.
These are sometimes referred to as English Blends, although that term is up for debate. I wouldn't recommend a heavy "Latakia Bomb" to start out with, as they can be a bit shocking or off-putting to the first-time smoker. Latakia is known for its rich, smoky taste, due to the process of smoke-curing that it undergoes during its preparation. Many associate Latakia with the smell of campfires.
Perique Blends Ah, Perique...my favorite. It can add that little something extra to so many different kinds of blends. Depending upon the types and proportions of the other tobaccos with which it is blended, it can be soothing or spicy. Many consider that it provides a dark fruit or aged flavor, which makes sense considering it undergoes a long anaerobic aging process. True Perique is only available from the St. James Parish of Louisiana.
Dark-Fired Kentucky Blends DFK starts out as Burley and undergoes a smoking/firing process similar to what is done to Orientals to create Latakia. However, I find Dark-Fired Kentucky to be less "campfire" tasting than Latakia, and more reminiscent of Grilled or BBQ'd meats. I love it!
Cigar Leaf Blends These blends will be right up the alley of those who are already cigar smokers. While they are typically stronger tasting and smelling blends than most pipe tobaccos, they are milder than most cigars due to the other, more typical pipe tobacco leaves implemented in the blend. Examples of these are Cornell & Diehl Gray Ghost, and GL Pease Key Largo. Oriental Blends These are crisp and somewhat tangy or even a slight bit sour tasting. Oriental leaf reminds me of seasoned meats, and are a bit exotic tasting. Blends that I think implement Orientals well are Savinelli Brunello Flake, and any of the Captain Earle's blends but specifically Honor Blend and Reflections. As I've found my own personal tastes, I've gravitated more towards blends that include some mixture of Burleys, Virginias, Perique and/or Dark-Fired...but that's just me. You may find that your taste in pipe tobacco is completely different from mine! If you enjoy smoking, I thoroughly believe there's something for everyone in the realm of pipe tobacco. I could include many more, but that's plenty enough to get you started down the yellow brick road that eventually branches in so many directions, you may never reach the Wizard of Oz! But that's kind of the point with Pipe Smoking...the journey is much more important than the destination. Enjoy! 
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