The Tolladay surname hails from England, and can be traced back as far as recorded information exists. The name itself has two possible meanings - neither of which have ever ben verified. Since a surname often indicated the trade of the individual who bore the name it may be that "Toll-A-Day" was derived from one who collects a toll - or tax. If that's the case, then the one who collected the toll may have also been a man to whom you would pay a toll for escort or access, across a bridge or river.
Since the surname is pronounced Tall-A-Day or the English accent equivalent Ta-La-Dee (which by the way explains why so many different variations of the spelling occured in America, it may have a different meaning altogether. That one I'm still researching. When I can - I will add more information on the history of the name.
The name Perry which has been handed down through the generations, also has a very interesting heritage. It seems the name Perry is derived from - son of Henry. In England, pre dating the Crusades, many who were named Henry were called by their nickname Harry. To introduce a son of Henry, you would say, "yon is hap-Harry" Spoken it sounds like "yon is Perry."