I doubt that will happen because not only Hit The Road belongs to LucasArts, but now it's Telltale the one that owns the rights to publish Sam & Max games.
So neither LucasArts nor Telltale can publish a remake of that game on their own. Unless they make some sort of agreement, that is. But I don't think LucasArts thinks it's financially viable to release a remake of that game, since they already cancelled its sequel some years ago.
The most likely next LA remake will be probably Monkey Island: LeChuck's Revenge </captain_obvious>