The latest in my ad hoc series on surname origins.
Based on: Reaney, P H, (ed. Wilson, R M), 1997, Oxford Dictionary of English Surnames, 3rd ed., OUP, Oxford, unless otherwise stated.
Underwood
Earliest in Andrew’s Kindred: John Underwood, father of Mary Underwood, baptised 25 January 1713, St Mary, Stafford, Staffordshire.

A dweller below a wood on a hillside, or from a place named Underwood, such as in Derbyshire or Nottinghamshire. There is a Weston Underwood about five miles north west of Derby.
Upton
Earliest in Andrew’s Kindred: Richard Upton, born about 1754, probably at Bishops Wood, Staffordshire.
From one of the numerous places named Upton.
Ushawood / Usherwood
Earliest in Andrew’s Kindred: John Usherwood, father of Elizabeth Usherwood, baptised 6 February 1687, Measham, Derbyshire.
This name is bundled up with Isherwood. “From an unknown place, probably in Lancashire”. The Internet Surname Database suggests derivation from a lost village in the parish of Bolton-le-Moors, Lancashire (today just Bolton). On the Ordnance Survey of 1844 is an Isherwood Fold, to the north east of Bolton. There seems to be no other landscape recollection at that time.