In my searches for info on the Skidmore family, I have found the online info on the Brunson and Faris/Phares families to be very helpful. There is a book availabe from Warren Skidmore and another from Jerry Alsup.
In a recent article concerning Joseph Skidmore of Randolph Co VA (now WV) some of the Skidmores left that area to go to the Tidewater region of VA or NC. From there they went into KY, TN, etc., whether through the Cumberland Gap or down the Ohio River. Some went on to GA, AL,and MS. Many of their descendants went on into MO,AR, OK, TX, OR and CA.
Happy hunting! Please keep in touch and I'll help when I can.