Note that both sentences are actually ungrammatical because a semicolon should only be used if what follows is an independent clause.
Replace the semicolon with a period, and you will see the problem. What follows the semicolon does not stand on its own as anything other than a sentence fragment.
But you can use a comma instead, where what follow it acts to modify what came before:
It used to be worse, with whole evenings of crying and yelling.
It used to be worse, with whole evenings spent crying and yelling.
It used to be worse, with whole evenings filled with crying and yelling.
The first sentence doesn't work so well:
✘ It used to be worse, with whole evenings crying and yelling.
On analysis (although it would likely be understood anyway), it sounds as if it's the evenings themselves that are doing the crying and yelling.
Even if you allow the semicolon to remain, the problem is the same. Without something before crying and yelling it has an effect similar to a misplaced modifier.