MLB draft begins tonight. Rounds 1 and 2

"Driveways" are an Americanized version of the English "Drive."  An actual "drive" or a "driveway" is much larger.  They were the drive up to a house.  With the explosion of the suburban jungle after World War II, driveways in America got shorter and shorter.  However, they were called "driveways" as a marketing ploy to help make the houses sound fancier than they actually are.

"Parkways" are an American invention.  Originally, "parkways" were designed to connect major roads with scenic areas, like parks.  Other roads were designated "parkways," because they went through parks.  Some of the parks and other scenic areas around those roads were subsequently destroyed, leaving several roads with the incongruent "parkway" designation.  Beginning with the early 20th century, starting in New York City, the term "parkway" began to be used for toll roads.  The reason this was done was because people associated "parkways" with travelling to or through a park or other scenic area.  Toll roads were named "parkways," because the toll road owners believed that more people would travel on a parkway, if it was named a "parkway."  Today, because of attempts to market, using the word "parkway," much of the original meaning has been lost.  

The long and the short of the genesis of the words is that driveways and parkways were used to refer to things that used to be awesome.  However, they were intentionally corrupted by shrewd businessmen, in order to bilk saps out of money.  The sense of the words has now become so corrupted that people point out the apparent contradiction, not knowing that they themselves have been hoodwinked into thinking that the words that they are using are actually referring to the things that they are trying to describe.