Thank you for your list of resources and links, it will keep me busy for while.

Your observation about the apprenticeship process was quite helpful, I had 
not actually put together the time frame of which you speak but it makes 
good sense to look at it in that manner.

I have tried the VA archives but have not yet found him, it is Richard Highfield 
I am looking for and there are various ways to spell his name that make it 
more difficult to locate any records on him. The name has been spelled 
Highfield/Highfill/Nysfield/Hughfield, etc.

Richard is listed on these records, along with 20 other individuals, all young 
and including females, as being bound to a certain Benjamin Johnson. Most of 
the individuals were bound for VA, some for Barbados. No shire is listed for 
Richard, just that he was 21 at the time.

I have no idea how to find a Headright for him, I just simply have not found 
anything on him in VA.

Richard was first found in St. Mary's County, MD, which is bordered by the 
Patuxent River, the Chesapeake Bay, the Potomac River, and the Wicomico 
River, and quite close to Virginia. You have raised a good point about the 
location, something I had missed, and have been quite helpful. Thank you,

Jeanine Scholz