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60 free Crosswords trivia questions with answers — trivia quiz, new questions added Aug 2026.
This crosswords trivia quiz covers the newspaper puzzle from its 1913 debut in the New York World to today's apps and tournaments. The easy questions are ones any solver can attempt: what across and down mean, the standard grid size, which day's New York Times puzzle is easiest, what a question mark at the end of a clue signals, and what to call someone who makes or solves crosswords. From there it moves through the history: Arthur Wynne, the 1924 Simon and Schuster book that started a craze, the Times editorial calling it a sinful waste, and the day the paper finally gave in during World War II. The harder end is for cruciverbalists: Torquemada, Ximenes and Afrit and the rules of fair cryptic clues, the Listener puzzle, Leonard Dawe and the D-Day codenames, Margaret Farrar, Will Weng, Eugene Maleska and Will Shortz, the enigmatology degree, the ACPT and Wordplay, the 1996 election-day puzzle, Sondheim bringing cryptics to America, crosswordese, Bletchley Park recruits and the ancient Sator Square. Every answer was checked against encyclopaedia entries on the crossword and its makers before publishing, and the supporting sentence is stored with each question. If you enjoy this one, try our word games, board games and newspaper history quizzes next.
30 of 60 questions with answers and explanations. Play the quiz
Q 01What are the two directions in which crossword entries run?
Across and down
Each white square usually takes one letter, and black squares separate the entries.
Q 02What is a person who constructs or solves crosswords called?
A cruciverbalist
The word was coined in the 1970s from the Latin for cross and word.
Q 03Who published the word-cross puzzle in the New York World on 21 December 1913 that is usually called the first crossword?
Arthur Wynne
He was a journalist who had played violin in the Pittsburgh Symphony Orchestra.
Q 04The first crossword appeared in which part of the Sunday New York World?
The Fun page
Wynne created the whole page of puzzles for that section.
Q 05In which English city was the inventor of the modern crossword born in 1871?
Liverpool
He lived on Edge Lane for a time before emigrating to the United States.
Q 06An earlier crossword-like puzzle titled Per passare il tempo appeared in 1890 in a magazine of which country?
Italy
Giuseppe Airoldi's puzzle was a four-by-four grid with no shaded squares.
Q 07Which publisher issued the first book of crossword puzzles in 1924?
Simon and Schuster
The idea came from co-founder Richard Simon's aunt, and the book launched the firm as a major publisher.
Q 08Which British newspaper was the first to publish a crossword, on 2 November 1924?
The Sunday Express
It was a Wynne puzzle adapted for the UK.
Q 09What did a 1924 New York Times editorial call the new crossword fad?
A sinful waste
The same paper did not run a crossword of its own until 1942.
Q 10On what date did The New York Times finally publish its first crossword?
15 February 1942
The puzzle was seen as a welcome distraction from the harsh news of World War II.
Q 11Who was The New York Times' first crossword editor, serving from 1942?
Margaret Farrar
She had edited the first crossword books and used the royalties to underwrite her husband's publishing house.
Q 12Who became the fourth editor of The New York Times crossword in 1993?
Will Shortz
He has also been the puzzle master on NPR's Weekend Edition Sunday since 1987.
Q 13Will Shortz, NYT crossword editor from 1993, holds the only known degree in what field?
Enigmatology
He graduated from Indiana University in 1974.
Q 21Which type of clue is usually the easiest in an American puzzle and a good place to start?
Fill-in-the-blank clues
For example, blank Boleyn gives ANNE.
Q 22Most American crossword grids are laid out with what property?
Rotational symmetry
Constructors place theme answers first, then fill the rest of the grid, then write clues.
Q 23What is the term for obscure words such as ETUI, ERNE and OLEO that appear far more often in crosswords than in life?
Crosswordese
They survive because their vowel-heavy letters help constructors fill grids.
Q 14Which sport is Will Shortz, NYT crossword editor from 1993, known to be skilled at?
Table tennis
He founded the American Crossword Puzzle Tournament in 1978 and directed it for decades.
Q 15Who was the second New York Times crossword editor, a former head of the paper's metropolitan copy desk?
Will Weng
Eugene Maleska followed him as third editor until 1993.
Q 16What is the standard size of a weekday New York Times crossword grid?
15 by 15
The Sunday puzzle is 21 by 21.
Q 17Which day's New York Times crossword is the easiest?
Monday
Difficulty rises through the week to Saturday; solvers use the day as shorthand for how hard a puzzle is.
Q 18The Sunday New York Times puzzle is about as hard as which weekday-size puzzle?
Thursday
It is bigger, not harder.
Q 19A question mark at the end of a crossword clue usually signals what?
A punning answer
The classic example clues what a grate might be full of.
Q 20What does the abbreviation Var. in a clue tell the solver?
The answer is a variant spelling
EMEER instead of EMIR is the standard example.
Q 24Which Observer setter used the pen name Torquemada, after the Spanish Grand Inquisitor?
Edward Powys Mathers
He set cryptics for the paper from 1926 until his death and also wrote the murder puzzle Cain's Jawbone.
Q 25Torquemada's successor at The Observer, who codified the rules of fair cryptic clueing in a 1966 book, set puzzles under what name?
Ximenes
His real name was Derrick Somerset Macnutt, head of classics at Christ's Hospital.
Q 26What was the day job of the Observer setter who wrote the 1966 rulebook on fair cryptic clues?
Head of Classics at Christ's Hospital
He had taken a double first in classics at Jesus College, Cambridge.
Q 27Which setter, writing as Afrit, set out the principle of fair cluing in Armchair Crosswords (1946)?
Alistair Ferguson Ritchie
He credited it to the fictional Book of the Crossword.
Q 28Introduced in 1930, which weekly puzzle is generally regarded as the hardest cryptic in a British national publication?
The Listener
It has been published in The Times since the magazine folded.
Q 29Which Daily Telegraph compiler was interrogated in 1944 after D-Day codenames such as Utah and Mulberry appeared in his puzzles?
Leonard Dawe
He was a schoolteacher and former Southampton amateur footballer.
Q 30Some cryptologists for which wartime codebreaking centre were recruited after doing well in a crossword competition?
Bletchley Park
Puzzle skill was seen as a marker of the right kind of mind.