Star Trek has been a staple in the world of comics dating back to the Gold Key days when Captain Kirk and crew, somewhat resembling their TV counterparts, took on strange new worlds in the days of the newsstand. Since that time, nearly every iteration of Star Trek has appeared in their own comic book--with the strange exception of Star Trek: Enterprise, which had the unfortunate luck of falling into a period when Trek comics were scarce.
The first Star Trek comic that I picked up was Star Trek: The Next Generation #43. It was in the middle of an arc, but it had great art, the saucer was separated from the star drive section, and the crew was trying to solve a mystery and reunite. I was very happy to have purchased the book--I believe at a local comic shop (there were a handful of those back then, now--the closest one is an hour drive. A good one is nearly two hours away). However, I recall going to a local card shop/book store (yeah, they had those, too, back then). And they still had Star Trek: The Next Generation #42 on their shelf! So, I not only got another part of the story I'd read in #43, but this had my favorite character, Dr. Crusher, on the cover!
While at the same store, I also picked up the latest Star Trek (original series crew) comic--#44.
It was a self-contained story about a so-called haunted planet. I'm sure I still have the issue in storage, but I may have to pick up another copy from eBay. So that was my first foray into Trek comics. The next major milestone that I recall from those days was Star Trek: The Next Generation's Borg arc, from 47-50. Not only were those great days of comics, but just at the cusp of the heyday that issued in eighteen years of non-stop Star Trek on TV and movies.