This is my second-earliest memory (after the day my sister was born):
Spring of 1993. I was about 2.5 years old, and my sister had just been born about two months earlier. Well, my Grandpa decided to take me to a train show down in Allentown. As I was waiting for my grandpa to come pick me up, my dad pulled me to the side and told me "Don't let Pappy buy you anything." Well, he came and picked me up, and Dad told him the same thing.
When we got the train show, first thing he did was offer to buy me a raffle ticket for the Thomas and James G gauge items. I said that he wasn't supposed to buy me anything, but he said it was okay, because it was cheap.
The next thing we did was walk into this room. To the left were boxes (starter set), and to the right was a man behind a counter. While my Grandpa was talking to the man, I just started at this box with a train on it. After a while, he asked me "Do you want that Michael?" How could I say no? lol. That box contained a Union Pacific Steam Freight Starter Set, and that set led to the last 19 years in the hobby (it's crazy for me to think that I have been in this hobby about as long as I have been using the bathroom!).
Although I don't have a photo of it when it was new, here is one from a few years later, with my second set, along with a few add on cars. This was probably 96 or 97: