"How come the shortest distance between two points is always under construction?” is a jocular line about driving that was published in Changing Times—The Kiplinger Magazine in November 1966. “New York is the only town where the shortest distance between two points is always under construction” was published in Parade magazine on August 17, 1969. “Getting around in a big city like New York wouldn’t be so bad, except the shortest distance between two points is usually under construction—Daisy Brown” was published in The Wall Street Journal on February 12, 1970.

The saying is sometimes credited to Atlanta (GA) Constitution columnist Leo Aikman (1908-1978), but the earliest citations do not credit any specific person. “‘The shortest distance between two points is under construction.“‘Noelie Altile” was posted on Twitter on June 4, 2007, but it’s also unlikely that Noelie Altito—the usual spelling—said it first. The saying has been printed on many images.


Google Books
November 1966, Changing Times—The Kiplinger Magazine, “Notes on these changing times,” pg. 2, col. 1:
How come the shortest distance between two points is always under construction?

6 December 1966, Aberdeen (SD) American-News, “Earl Wilson’s New York,” pg. 4, col. 5:
EARL’S PEARLS: Sometimes it seems that the shortest distance between two points is always under construction.

6 March 1967, Austin (TX) Statesman, “Wray Weddell’s Austin,” pg. 1, col. 1:
From the Texas Tourist Council Newsletter: (...) “How come the shortest distance between two points is always under construction.”

27 April 1969, Boston (MA) Globe, “My Favorite Jokes” by Michael Allen, Parade magazine, pg. 31, col. 1:
Most of the time the shortest distance between two points is under construction.

17 August 1969, Boston (MA) Globe, “My Favorite Jokes” by Steve Rossi & Slappy White, Parade magazine, pg. 31, col. 1:
New York is the only town where the shortest distance between two points is always under construction.

12 February 1970, The Wall Street Journal (New York, NY), “Pepper...and Salt,” pg. 8, col. 1:
Obstacle Course
Getting around in a big city like New York wouldn’t be so bad, except the shortest distance between two points is usually under construction.
-- Daisy Brown.

Google Books
Murphy’s Law
By Arthur Bloch
New York, NY: A Perigee Book
2003
Pg. 157:
Hyman’s Highway Hypothesis
The shortest distance between two points is usually under construction.

Google Books
Business Wit & Wisdom
By Richard Zera
Washington, DC: Beard Books
2005
Pg. 262:
When traveling by car, the general rule is that the shortest distance between two points is under construction.

Twitter
Maarten Cannaerts‏
@maartenc
“The shortest distance between two points is under construction.” Noelie Altile…
8:29 AM - 4 Jun 2007

Google Books
The Official Rules:
5,427 Laws, Principles, and Axioms to Help You Cope with Crises, Deadlines, Bad Luck, Rude Behavior, Red Tape, and Attacks by Inanimate Objects
By Paul Dickson
Mineola, NY: Dover Publications, Inc.
2013
Pg. 225:
McGregor’s Revised Maxim. The shortest distance between two points is under construction. (Scott D. McGregor, Moscow, Idaho.)

Google Books
The Real Hitchhikers Guide
By Jack Mikkel Revheim
Lulu Press (Lulu.com)
2014
Pg. ?:
Leo Aikman, a columnist for the Atlanta constitution from 1946, once said «The shortest distance between two points is under construction».

Jokes Explained
The shortest distance between two points
January 11, 2017
The shortest distance between two points is under construction
(...)
The humor in this joke lies in the fact that the original phrase has been modified to become a pessimistic statement about travel. The assumption that you will always travel slower to any given place than you could go is humorous.