To trailer or not to treailer??

Alright guys since it's getting closer and closer to my show season I was wondering what everyone's "rule" on trailering a vehicle is. Is there a certain distance you travel before you trailer it, or is it just to look "cool" when you roll up on a trailer? I am thinking about trailering mine to Showfest since it's like 4 hours away and want to know everyone's opinions...Chris