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On average, the state with the highest paying trucking jobs is Mississippi with an average of $68,000 per year. A lot of heavy hauling and long haul positions are available which require additional skill and experience. The next state on the list is Wyoming at $61,000.
Highest Paying Truck Driving Jobs. It is no secret that over the road, or OTR, truck drivers make the best money. Walmart is one of the highest paying, with an average salary of $71,500 per year before bonuses.ighest Paying Truck Driving Jobs. It is no secret that over the road, or OTR, truck drivers make the best money. Walmart is one of the highest paying, with an average salary of $71,500 per year before bonuses.