The Jessup's have lived in the valley bside the third hilltop for generation. Patriarch James Jessup was the first free slave to settle and make his roots. He bought massive amounts of land and staked claim to many for more land in the west.

The Jessups are the wealthiest family in the valley. For over a century now the Beaudrey 's have paid rent to the Jessup's to grow their grapes.