The first home run I remember seeing hit in person on the little league field was by Al Baker. He parked one into the trees in centerfield. I think the trees are still there today.
The first softball home run I remember seeing hit was by Tony Holland, which came several years before the famous collision and subsequent brawl at home plate with the late Fred DeLoach.
There hasn't been too many Pee Wee League (over the fence) homers in recent years, but 7-year-old Graham Futrell of the Yankees smacked a homer in a game last week.
Congrats to Graham, the son of Stacey and Janay Futrell. He now has tied me for career, all-time homers hit at the Complex. One. And he still has his best baseball in front of him.