What does the phrase “to pull up stakes” mean and Where does it originate?

The phrase “to pull up stakes” means: To move from a place; change one’s location.

This takes us back to colonial days in New England, to the time when a settler, dissatisfied for any cause with the parcel of land allotted to him, took up the boundary stakes and either returned to England or moved to another location of his own choosing.

The earliest citation is to an English lawyer, Thomas Lechford, who, after a stay of two years in Boston, 1638 to 1640, wrote to a friend in England, “I am loth to hear of a stay (in New England), but am plucking up stakes, with as much speed as I may, if so be I may be so happy as to arrive in Ireland.”