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Enslaved laborers cultivated tobacco, wheat, and other grains as the primary crops at Monticello during Thomas Jefferson's lifetime. The following chronology records the transition from tobacco to grains.

1740s-1769: Monticello, as we know it today, was a part of Shadwell farm, the birthplace of Thomas Jefferson. At that time, it was a 3,000-acre tobacco plantation, established by Peter Jefferson in the early 1740s. Tobacco plants required very intensive labor and had a damaging effect on the soil. Of the 50 enslaved individuals on the plantation at the time, 30 lived and worked on the Shadwell farm. Due to the nature of the tobacco plants, the plantings were generally small and moved after several seasons. In many cases, the tobacco plants would be replaced by corn.

1770-1790: Tobacco remained the chief crop at Monticello during this time period. However, the number of enslaved individuals drastically increased from 50 in 1770 to 125 by 1783, the year that Jefferson left for France.

1790-1808: After returning to Monticello in 1793, Jefferson directed his enslaved laborers away from tobacco cultivation and on to grains. Grains required less labor but greater organization, and skill was essential for their success. 105 enslaved individuals labored at Monticello to ensure the wheat crops' success.

1809-1826: The main crop at Monticello continued to be wheat and other grains until Jefferson's death on July 4, 1826. At the time of his death, approximtely 200 enslaved people lived and worked on the grounds on the mountaintop.

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