Woods is believed to have come to the area about 1734 from Pennsylvania, and to have acquired substantial land holdings in the area from Woods Gap to Meachum's River, and along Ivy Creek. Richard Woods, for whom "Dick Woods Road" is named, is thought to be a kinsman of Michael, and by some, a son. (He's not mentioned in Michael's will, so this is unlikely.) In anycase, the term "DS" eventually came to indicate the area, rather than the specific tree or location. For example, a Presbyterian congregation in the area was given a parcel of land on which the DS Meetinghouse Stood.
From:ALBEMARLE COUNTY IN VIRGINIA, by Rev. Edgar Woods, 1901, pp. 319-320
“Among the earliest settlers in the western part of the county, who came as is said under the leadership of Michael Woods, was a family named Stockton. Though their name has entirely disappeared, they have in a number of ways left their mark behind. They consisted of several branches. They erected perhaps the first mill in that section of the county. The north fork of Mechum's River still bears the name of Stockton's Creek, the south fork in early times was called Stockton's Mill creek, and the first name by which Israel's Gap was known was Stockton's Thoroughfare. The famous abbreviation of D. S. is also ascribed to the head of the family. One story recites that Michael Woods and Davis Stockton landed at Williamsburg, and came to the wilds of Goochland together, that arriving at D. S., they advanced in different directions, Woods continuing straight forward to Woods's Gap, and Stockton bearing to the left along the foot of the mountain towards Batesville, and that as a memorial of the place where they separated, Stockton carved his initials on a tree . . . Woods's home lay at the mouth of Woods's Gap, and the Stocktons were settled along Mecham's River, the south fork as well as the north.