He really is much safer in the crate during your car ride!
I have a 7 month old lab and I would just let him sleep wherever we were. He knows when we are asleep, it's his sleepy time too.
Otherwise I'd put him in his crate in the pick up truck. I don't know about America, but in Australia there is no way I'd leave my dog in a crate outside over night - god knows what could get in and bite him!
I'd keep him in the bed with you or in the truck in the crate. I would not leave him in the crate next to the truck where he would be helpless. Of course, I don't know where you are going and the dangers from wildlife vary (raccoons, javelina, bear, wild hogs . . . ) but you don't want to leave him unprotected and vulnerable.
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