Tennis Matches with High School Player

Hi all,  I enjoy watching tennis but don't play myself.  My son is 17 years old and plays on his high school team in Windsor, Va.  I am interested in getting him together with other players that can help him improve.  Would particularly like to keep him playing this summer and fall.  He has played in a few tournaments on the Peninsula and has played at the 3.5 level but I would also like to see him play some players in the 4.0 range to help him improve.  Could play in Suffolk, Chesapeake, Newport News,Hampton or Williamsburg.