Answer:

WAGONER

Answer	Crossword Clue
WAGONER	Oater driver, maybe
WAGONER	Conestoga driver
WAGONER	Western driver

WAGONER	Charles's Wain.
WAGONER	Conestoga boss
WAGONER	Oregon Trail traveler, e.g.
WAGONER	One who may be in charge of a team
WAGONER	Porter who played with Parton
WAGONER	Charioteer