The winding walk defines the perimeter of the leveled, oval-shaped West Lawn. The "smooth, level" lawn was a favorite playground for the children, although the earliest images of the West Front of Monticello reveal a weedy, disheveled surface. The lawn was probably scythed once or twice a year and its appearance inevitably reflected the pre-lawn mower technology of the early nineteenth century.
While there is a reference to sheep browsing on the choice orange trees Jefferson cultivated in the nearby green house, it is doubtful he would allow them to graze on the lawn in such proximity to his flower borders. Edmund Bacon, a Monticello overseer, was instructed in 1808 to manure the "grass grounds" around the house. Instead, he mistakenly covered the lawn with a heavy covering of charcoal. At times, grounds keeping at Monticello seemed like a comedy of errors.