In August, 1808, finding a prospect of selling his Maryland lands, he formed a project of carrying his sixty slaves to Mississippi and hiring out some of them there until a new plantation should be ready for routine operation.

He further contemplated taking with him ten or fifteen families of non-slaveholding whites who were eager to migrate under his guidance and wished employment by him for a season while they cast about for farms of their own.

Covington accordingly sent inquiries as to the prevailing rates of hire and the customary feeding and treatment of slaves.

He asked whether they were commonly worked only from "sun to sun," and explained his thought by saying, "It is possible that so much labor may be required of hirelings and so little regard may be had for their constitutions as to render them in a few years not only unprofitable but expensive." He asked further whether the slaves there were contented, whether they as universally took wives and husbands and as easily reared children as in Maryland, whether cotton was of more certain yield and sale than tobacco, what was the cost of clearing land and erecting rough buildings, what the abundance and quality of fruit, and what the nature of the climate.
The replies he received were quite satisfactory, but a failure to sell part of his Maryland lands caused him to leave twenty-six of his slaves in the east.

The rest he sent forward with a neighbor's gang.