Not counting Too Many Games, which was like an 8 hour drive. I've gone across state lines just checking store inventories before. Hell, I've spent an entire day driving around to every known Family Dollar location within a couple of hours away, just to check their random buyout inventories when I first found out about those. I've drove across state lines to check GameStop stores. I've drove all across the state, and some of a neighboring state just to check pawn shops, various game stores I don't have near to me, flea markets. I used to routinely drive about 3 hours to an out of state flea market on the weekends. So yeah, I've done stuff like that a lot.
Any time I go out of town there's lots of food and shopping which is not commonplace to me, living in a fairly small town. So the trips are usually worth it, just to stop by a sandwhich shop, and check out stores like Best Buy which I've never had in my home town.