A History of Short Words

From the New York Times Crossword Puzzle

PONY

Sun, 1 Feb '26
Small keg size
Tue, 31 Dec '24
Yankee Doodle's method of transport
Sun, 25 Jun '23
Carnival ride
Fri, 16 Jun '23
Small drinking glass, as for liquor
Wed, 23 Jun '21
One providing a ride at a fair, maybe