i have attended quite a few whiskeyfests in new york and highly recommend going if you at all like whiskey. i would also recommend deciding what you're most interested in tasting before you go, as the selection can be quite overwhelming, even to a seasoned professional. in recent years there have also been beers and tequilas offered, but i've never made it over to those tables. pace yourself and drink lots of water!
No experience with the Fest, if you are into Rye, try to score some Old Potrero Hill small batch Rye made in S.F. still made on, I believe, Potrero Hill. All whiskey, in my option, should be as old as you can find it, sipped neat. For a "fun:" and young bourbon, try Cabin Still - cheap but playful.
I've been to the one in New York a few times. Go. The selection of bourbon will be fairly broad. Rye, well there just is not that much rye made, but most of what is available will be there. There will be a bit of Irish, and if it is there, have some Red Breast, if you have not otherwise had it. There will also be a number of others, not Scotch, bourbon, rye, etc. that are whiskeys or whiskys.
But the Scotch, the Scotch will be there in abundance. General rule: check out the models serving the Cutty Sark, but get your wee drams from the fat guy wearing a kilt. He has good stuff, in many cases. But the amount of different things you can taste is about as limited as your personal capacity. I nice had about 25 or so different whiskys. But that's a mere fraction of what is there. Have the rare expensive stuff, don't mess with cheap stuff. Cask strength is there, often from places that stopped making whisky. I had Linlithgow there a few years ago, about 120 proof, from a defunct Lowland distiller, and it tasted wonderful. I've learned a lot to by talking with the people who are representatives. Let them talk, nod your head, drink the whiskey, you'll learn.