Family History and Genealogy Resources by Surname
Woolsey Surname Origin
(Locality). That is, the Wolds-ley, from wold, a wood, a lawn, and sometimes a plain, and lle, or ley, a place.
Source: An Etymological Dictionary of Family and Christian Names With an Essay on their Derivation and Import; Arthur, William, M.A.; New York, NY: Sheldon, Blake, Bleeker & CO., 1857.
Woolsey Surname Meaning and Family Facts
There is more to Woolsey family history than the origin of your surname:
A Woolsey Family History Thought:
Whenever there's a will, you'll see an heir loom.