Picking gears

For me highway is no big deal
I live just outside of Toronto, even if I do highway it into T.O. its for 10-15 mins max.
Now to go to the drag park from here is a different story it's a couple of hours away.

I'm torn with going straight to 4.30 and maybe go overdrive over winter or compromise with 3.55/3.73/3.91.

I would like to do some traveling with the car but could always swap in 2.96 before hand if I don't go O.D.