Among the few settlers of German ancestry in the area that would become Durham County, Daniel (or David) and John Umstead, likely brothers, emigrated from Pennsylvania to North Carolina and settled along the Flat River and its tributary, Dial Creek in the mid-eighteenth century. The earliest recorded Umstead land transaction is a 1797 grant to David Umstead for an 18-acre tract on the Flat River some 1.5 miles north of the present village of Bahama that included a "mill house.”
A son of John Umstead, Squire D. (Daniel or Dewitt) Umstead married Martha Waller in 1835, and by 1850 had established himself as a prominent miller and farmer. That year the Orange County Population schedules reveal that the couple (then 38 and 33 years old respectively) were parents of eleven children (North Carolina Governor William B. Umstead was among their grandchildren) and owned four separate tracts of land in northeastern Orange County totaling 864 acres. The largest and presumably the home tract contained 650 acres. On this land, the Umsteads grew 6,000 pounds of tobacco, 500 bushels of corn, 200 bushels of wheat, and maintained $1,800 worth of livestock that included a herd of 30 swine. The other tracts, totaling 14 acres, 100 acres, and another 100 acres, may have been leased or farmed by other family members since no crops or livestock are recorded in the agricultural census for that year. The 14-acre tract (4 improved, 10 in woodland) was valued at $500, an unusually high value that may have reflected a commercial use, perhaps as a mill tract. [Orange County Agricultural Census, Mangum Township, 1860] Umstead's tobacco farm was a notably large one. Prior to the Civil War, typical North Carolina and Virginia tobacco farms rarely exceeded 300 acres and the vast majority were less than 50 acres.
By 1870 the Orange County Population Schedules, list Martha Umstead, widowed and then age 52, as the head of her household. It appears that as her sons married and established households, they were given tracts of land subdivided from her extensive holdings on which they built or remodeled a number of notable houses now in the Bahama area