“The older a man gets, the farther he had to walk to school as a boy” is a joke based on fathers who embellish their alleged hard scrabble beginnings. The kids today have it easy; the fathers had to walk five miles to school, without any shoes, uphill, through the snow, and so on.
 
“The older a man gets the farther the distance he had to walk to school as a boy” has been cited in print since October 1958 and is of unknown authorship. The 1962 citation, below, credits the cartoon “Abe Martin of Brown County” by Kin Hubbard (1868-1930), but no such cartoon has been located.
 
“I used to walk five miles to and from school, uphill both ways” is a similar joke.
 
   
12 October 1958, Florence (SC) Morning News, pg. 6B, col. 6:
The older a man gets the farther the distance he had to walk to school as a boy.
 
1 November 1958, Terre Haute (IN) Star, “It HappenedLast Night” by Earl Wilson, pg. 4, col. 5:
Wish I’d Said That—The older a man gets the further he had to walk to school as a boy.
 
18 November 1958, Janesville (WI) Daily Gazette, “Smile for Today,” pg. 1, col. 1:
The older a man gets, the further he had to walk to school as a boy.
     
17 July 1960, Trenton (NJ) Sunday Times-Advertiser, pg. 8, col. 2:
Story Expands
Bob Rockwell of “Man From Blackhawk” quips that the older a man gets the farther he had to walk to school as a boy!
 
Google News Archive
16 November 1960, Florence (AL) Times, “Jack and Jackie Make Quite A Headline Duo” by Ben Knight, pg. 2, col. 6:
The older a person gets, the further he had to walk to school as a boy.
 
Google News Archive
14 December 1960, Youngstown (OH) Daily Vindicator, “Today’s Chuckle,” pg. 39, col. 4:
The older a man gets, the farther he had to walk to school as a boy.
     
Google Books
Portrait of a President:
John F. Kennedy in Profile
By William Manchester
Boston, MA: Little, Brown
1962
Pg. ?:
Like many tycoons he has sometimes tended to exaggerate his humble origins — as Abe Martin observed, the older a man gets, the farther he had to walk to school as a boy — yet he had a point.
 
Google News Archive
You’re Never Too Old to Laugh:
A Laugh-Out-Loud Collection of Cartoons, Quotes, Jokes, and Trivia on Growing Older
By Ed Fischer
Minnetonka, MN: Meadowbrook Press
2012
Pg. ?:
The older a man gets, the farther he had to walk to school as a boy.
—Anonymous