It's one of the head-scratchers of the English language: As comedian George Carlin pointed out, "parkway" and "driveway" don’t quite make sense, but we understand them all the same. Non-native English speakers might stumble over this idiosyncratic language twist, but the confusion is easily cleared up.
Parkway is an Americanism that dates back to 1885, meaning “an open landscaped highway.”
Driveway is another uniquely American term that can be traced back a few years earlier, to 1865. It refers to “a short road leading from a public road to a house or garage.”
Why do we drive on the parkway but park in a driveway?
The origin dates of these words give a clue as to the confusing usage. For most of the 1800s, cars didn’t exist, so driving or parking a car wasn't even an option. Instead, "parkway" was related to the other definition of "park" — an open space with trees, flowers, and other greenery. The definition evolved over the years (notably following the invention of the automobile) into a scenic road lined with trees and grass.
Historian Kirk Savage traced the evolution of the parkway in his book “Monument Wars.”
“In the nineteenth century, to park meant to plant a tree or spread a patch of turf or flowers — to create a little patch of parkland. In Washington, the Parking Commission was a group of respected horticulturalists who supervised street-tree planting. On the city’s wide streets, parking places typically referred to strips of grass, flowers, or trees planted alongside the pavement, or in the larger squares or circles. These strips of parking not only cooled the streets but made them more manageable by reducing their great width and the amount of paving they required. By the turn of the century, such parking areas were sometimes used to hold horse-drawn carriages on special occasions; these were temporary intrusions that did not threaten the parkland itself. When automobiles started to overrun cities in the early twentieth century, parking areas were given over to car storage and the word began to refer to the cars themselves rather than the trees and grass they were replacing.”
Driveways have been around a bit longer, with a more consistent definition, but they used to be applicable to the horse and buggy. When "driveway" came into use, they were longer paths one would drive down to connect the private property to a public road. Nowadays, it’s usually just a short stretch of pavement connecting your house to the road, but the primary use of a driveway is for, well, parking your car.