Trucking would be the fastest but spring is prime time, so unlikely to find an empty truck headed NB.
Most logical
route:
Hudson to Erie Canal, Lake Erie, Huron to Michigan. (must get under 15.5' air draft)
Reasonable Alternative 1:
Hudson to Erie Canal, cut off at Oswego, the up
Ontario to Lake Erie, Huron to Michigan.
Reasonable Alternative 2: Hudson to Erie Canal, Cut off at Oswego, then jump across to the Trent Severn Canal and out at the north end of Huron.
Reasonable Alternative 3: Hudson to Champlain Canal, to St. Lawrence then up
Ontario with similar options.
Less Reasonable Alternative 1: The long way around to the St. Lawrence then similar to alternative 3.
Less Reasonable Alternative 2: South to the Gulf and then up the river system (upstream in a sailboat on the
mississippi section of the rivers is likely a non-starter).