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50 free Riddles and Brain Teasers trivia questions with answers — trivia quiz, new questions added Aug 2026.
Riddle trivia in two flavours. About half of these 50 questions hand you a classic riddle and four possible answers: the Sphinx's creature with one voice, Samson's eater that gave something to eat, the featherless bird on the wall, the twelve-spoked wheel with 720 sons, and the man with seven wives on the road to St Ives. The other half are brain teasers and trivia about riddles themselves: why you should switch doors in the Monty Hall problem, where the missing dollar went, who really wrote 'Einstein's riddle', and what Gollum wagered against Bilbo. It is built for quiz nights, classrooms and long car journeys, and it works for anyone from a sharp ten-year-old to a logic-puzzle veteran. Every question has one right answer and a short explanation that gives away the trick, so you learn the riddle as well as the answer. Every answer is checked against a cited source before publishing, so the solutions here are the accepted ones rather than internet guesses.
30 of 50 questions with answers and explanations. Play the quiz
Q 01What was Oedipus's answer to the Sphinx's riddle of the four-, two- and three-footed creature?
Man
A person crawls as a baby, walks upright as an adult and leans on a stick in old age.
Q 02In some accounts the Sphinx asked a second riddle: which two sisters each give birth to the other?
Day and night
Day and night: each gives birth to the other in endless turn; both words are feminine in Greek, which makes them 'sisters'.
Q 03What did Samson's riddle 'Out of the eater came something to eat, and out of the strong came something sweet' describe?
Honey in a lion's carcass
Honey in a lion's carcass: Samson had killed a lion and later found bees and honey in its body (Judges 14); the Philistines got the answer only by pressing his wife.
Q 04What was the answer to the riddle that probably became the nursery rhyme 'Humpty Dumpty'?
An egg
The trick relied on 'humpty dumpty' also being 18th-century slang for a short, clumsy person, who might survive a fall where an egg would not.
Q 05In 'As I was going to St Ives', what is the usual trick answer to how many were going to St Ives?
Just one
Only the narrator is actually said to be heading there; the man and his entourage are simply met on the road.
Q 06If everyone in the St Ives rhyme, kits and all, were going to St Ives, how many would that be including the narrator?
2,802
2,802: the narrator, the man, 7 wives, 49 sacks, 343 cats and 2,401 kits add up to 2,802.
Q 07In Wonderland, what answer does the Hatter give to his own raven and writing-desk riddle?
He hasn't the slightest idea
He hasn't the slightest idea: in the book the Hatter admits 'I haven't the slightest idea'; Carroll only invented an answer in an 1896 preface, and Sam Loyd offered 'Poe wrote on both'.
Q 08In Turandot, what is Calaf's answer to the riddle 'born each night, dying each dawn'?
Hope
Hope: Calaf answers 'la speranza', the thing that is born each night and dies each dawn, and goes on to solve Turandot's remaining two riddles.
Q 09What answers Turandot's second riddle: 'flickers red and warm like a flame, but is not fire'?
Blood
Blood: Calaf answers 'il sangue', which flickers red and warm like a flame yet is not fire, and grows cold when you die.
Q 10What is the 'featherless bird' that lands on a wall until the wind blows it off in the Central European riddle?
A snowflake
The 'wind' is really the sun's warmth in some versions, melting the flake away.
Q 11In the widespread riddle 'White field, black seeds', what are the field and seeds?
A page and its letters
A page and its letters: the white field is the page and the black seeds the letters; the Veronese Riddle (c. 800) adds oxen for the fingers and a plough for the pen.
Q 12What does a Rig Veda riddle mean by a 'twelve-spoked wheel, upon which stand 720 sons of one birth'?
The year
The year: its twelve months are the spokes, and 360 days plus 360 nights make the 720 'sons of one birth' (Rig Veda 1.164.11).
Q 13What animal does the medieval riddle 'Four hang, two point the way, two ward off dogs, one dangles behind' describe?
A cow
Q 21Which logician named the Knights and Knaves puzzles, where knights tell the truth and knaves lie, in 1978?
Raymond Smullyan
Raymond Smullyan coined 'knights and knaves' in his 1978 puzzle book What Is the Name of This Book?, where knights always tell the truth and knaves always lie.
Q 22On the island of knights and knaves, why can no inhabitant say 'I am a knave'?
Whether honest or dishonest, the speaker would contradict their own nature
Whether honest or dishonest, the speaker would contradict their own nature: a knight saying 'I am a knave' would be lying, and a knave saying it would be telling the truth.
Q 23In George Boolos's 1996 'Hardest Logic Puzzle Ever', the gods True, False and Random answer only in which words?
A cow: four teats hang, two horns point the way, two hind legs ward off dogs and the tail dangles behind; a 13th-century Icelandic version appears in Hervarar saga.
Q 14In the German riddle where Two-legs sits on Three-legs holding One-leg, what is Three-legs?
A stool
A stool: Three-legs is the three-legged stool that Two-legs (a person) sits on; Four-legs is the dog and One-leg the ham hock they fight over.
Q 15In Rumpelstiltskin, what must the queen do within three days to keep her child?
Guess the imp's name
Guess the imp's name: she has three days to name him, and succeeds only because her messenger overhears him singing 'Rumpelstiltskin' at his fire.
Q 16In the Monty Hall problem, what are your odds of winning the car if you switch doors?
2/3
2/3: switching wins whenever your first pick was wrong, which happens two times in three; Marilyn vos Savant's 1990 Parade column saying 'switch' drew thousands of angry letters.
Q 17In the missing dollar riddle ($30 paid, $3 back, bellhop keeps $2), where does the 'missing' dollar go?
Nowhere: the $27 already includes the $2 tip
Adding the tip to the $27 double-counts it; $25 in the till plus $2 tip is the $27 the guests paid.
Q 18In the classic wolf, cabbage and third-passenger river puzzle, which passenger crosses first?
The goat
The goat: it is the only passenger that cannot be left with either of the others, so it crosses first; the puzzle appears in Alcuin of York's Propositiones around 800.
Q 19What is the minimum number of moves needed to solve a Tower of Hanoi puzzle with three disks?
7
7: the minimum is 2 to the power n, minus 1, so three disks take 2^3 - 1 = 7 moves; 64 disks would take about 585 billion years at one move a second.
Q 20Who invented the Tower of Hanoi puzzle, first sold in 1883?
Édouard Lucas
Édouard Lucas, a French mathematician, sold the puzzle in 1883 under the anagram 'N. Claus de Siam'; the booklet's tale of Brahmins moving 64 golden disks was a story sold with the puzzle.
Da and ja
Da and ja: the gods answer every yes-no question in their own language, and you do not know which of 'da' and 'ja' means yes.
Q 24The Zebra Puzzle is often called whose 'riddle', despite no evidence he wrote it?
Albert Einstein
Albert Einstein: the puzzle is often called 'Einstein's Riddle', yet the 1962 Life International version names cigarette brands such as Kools that did not exist in his boyhood.
Q 25In the bridge and torch puzzle with crossing times 1, 2, 5 and 8 minutes, what is the fastest total in minutes?
15
15: 1 and 2 cross (2), 1 returns (1), 5 and 8 cross (8), 2 returns (2), 1 and 2 cross (2), so the two slowest never cross separately.
Q 26The nine dots puzzle asks you to join a 3×3 grid with how many straight lines without lifting the pen?
Four
Four: the nine dots can be joined with four straight lines only by extending them beyond the square, a solution often linked to the phrase 'thinking outside the box'.
Q 27The 2015 viral logic puzzle 'Cheryl's Birthday' came from a maths olympiad in which country?
Singapore
Singapore: the puzzle came from the 2015 Singapore and Asian Schools Math Olympiad; its answer is July 16, and it went viral after a TV presenter posted it as a primary-school question.
Q 28Which paradox says an expected-value calculation suggests you should always swap, though the choices are symmetric?
The two envelopes problem
One envelope holds twice as much as the other; the flawed argument says switching gains double while only risking half.
Q 29Which psychologist coined the term 'lateral thinking' in 1967?
Edward de Bono
Edward de Bono introduced 'lateral thinking' in his 1967 book The Use of Lateral Thinking, contrasting it with step-by-step 'vertical thinking'.
Q 30A riddle whose answer is a joke punchline, like 'Why did the chicken cross the road?', is called what?
A conundrum
A conundrum does not expect you to know the answer; it is a set-up for the gag.