James Winchester’s father founded, planned, and platted the town of Westminster, Maryland - the place of Winchester’s childhood home White Level.
Perhaps, taking after his father, Winchester set out to build towns as well. He began with Cairo, now lost to time, but once a bustling flatboat town with four doctors, two schools, thirteen stores, a cotton mill, woolen mill, gristmill, saw mill, still house, carpenter, cooper, blacksmith, silversmith, boatyard, shoemaker, tanyard, cotton spinning factory, church, Bell tavern, race track, and two large warehouses.
At the same time that Winchester was planning Cairo, he was also investing in Memphis along with his friends and business partners, Andrew Jackson and John Overton. Overton and Winchester would remain invested in Memphis over the years and Winchester’s first son Marcus Winchester served as the first mayor of Memphis. Winchester would pass away before seeing Memphis become a success.