Words at Play

Why Do We Park in the

Driveway and Drive on the
Parkway?
Finally, the answer to one of
life's enduring questions
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English is full of seeming contradictions:  ravel  means

both "to knit up" and "to unknit,"  inflammable refers to
something that's flammable, and so on. George Carlin, the
late comedian, often poked fun at English, and in doing so,
highlighted another one of these contradictions: why do
we park on the driveway but drive on the parkway?

The word 'parkway' originally referred to a broad road

through a park. Like 'driveway', it predates the
invention of the car.

First, a defining of terms. A  driveway  is "a private road

giving access from a public way to a building on abutting
grounds," and in America, we tend to park our cars in the
driveway since driveways typically come right alongside
one's house. A  parkway , on the other hand, is "a broad,
landscaped highway." The origins of each of these words
seems pretty clear— drive  +  way , and  park  +  way —but if
that's the case, when why don't the verbs that are the
originating point for each word ( drive  and park ) match up
with the meaning of the derivative noun? In short: we
don't drive on driveways, and we don't park on parkways.
What gives?
English is secretly serpentine: what looks like a straight
line between words sometimes isn't. That's the case with
with both  driveway  and  parkway .
Both words came into written use in the 1800s, long
before cars were even a glimmer in Henry Ford's
eye.  Parkway  originally referred to a broad road through
a park:
The most important improvement made of late in the
general plan of cities has been the introduction or
increase in number and breadth of parkways.
—  American Cyclopedia , 1875

So there's the connection between parks and  parkway ,

but why do we drive on them? Parkways were the perfect
places to  drive  a carriage down for a scenic jaunt out.
Once automobiles came on the scene, parkways became
the province of the car.
Driveway  came into written use a bit earlier
than  parkway  did. Unlike  parkway , the
word  driveway didn't refer to where the path was (a drive),
but what the path was for (driving). The earliest driveways
were roads that ran alongside barns, where vehicles like
wagons could drive up and either offload cargo (like hay,
food, or livestock) or take on cargo (like hay, food, or
livestock):
The building should be so placed that the barn floor could
be laid upon the beams, and the drive-way be into the end
directly under the roof. 
— Henry Colman,  Second Report on the Agriculture of
Massachusetts , 1839
Of course, these access roads onto a property became
handy places to park vehicles, and when the automobile
age began, these off-street roads became ideal places to
park the family car.

In time, the verbs that we used

with  parkway  and  driveway  became fixed—
drive  with  parkway  and park  with  driveway . And George
Carlin's stand-up routine about the nonsensical nature of
English gained one more data point.