Riddles and Brain Teasers Trivia
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60 free Riddles and Brain Teasers trivia questions with answers — trivia quiz, new questions added Oct 2026.
Riddle trivia in two flavours. About half of these 60 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 60 questions with answers and explanations. Play the quiz
Q 01What was Oedipus's answer to the Sphinx's riddle about what goes on four feet, then two, then three?
Man
Man: a baby crawls on all fours, an adult walks on two legs and the old lean on a stick. In the usual telling the beaten Sphinx then threw herself from her rock and died.
Q 02Which two sisters 'each give birth to the other' in a riddle from an ancient Greek tragedy about Oedipus?
Day and night
Day and night: each gives birth to the other in endless turn, and both words are feminine in Greek, which makes them sisters. Some later accounts make it a second riddle of the Sphinx.
Q 03What did Samson's riddle 'Out of the eater, something to eat' 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
An egg: the riddle probably played on 'humpty dumpty' being 18th-century slang for a short, clumsy person, who might survive a fall from a wall where an egg would not.
Q 05In the traditional answer to the riddle 'As I was going to St Ives', who is going to St Ives?
Just the narrator
Just the narrator: the man, his wives and their sacks, cats and kits are only met on the road, so they are taken to be coming the other way and all the sevens are a decoy.
Q 06Which mathematician's book Liber Abaci has a sevens puzzle much like the rhyme 'As I was going to St Ives'?
Fibonacci
Fibonacci: his Liber Abaci of 1202, the book that introduced Hindu-Arabic numerals to much of Europe, repeats the old sum of sevens. Counted in full, the St Ives rhyme comes 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: when Alice gives up, the Hatter admits it, the March Hare adds 'Nor I', and she tells them off for wasting time on riddles that have no answers.
Q 08In Turandot, what is Calaf's answer to the riddle 'born each night, dying each dawn'?
Hope
Hope: 'la speranza' is the first of Calaf's three right answers. A suitor who gets one wrong loses his head, as the Prince of Persia does in Act 1.
Q 09What answers Turandot's second riddle: 'flickers red and warm like a flame, but is not fire'?
Blood
Blood: 'il sangue' is Calaf's second right answer. The third riddle, about ice that kindles fire, turns out to describe Turandot herself.
Q 10In an old German riddle, what is the 'featherless bird' that a mouthless woman eats off a leafless tree?
A snowflake
A snowflake: the leafless tree is a tree in winter and the mouthless woman is the sun, which 'eats' the snow by melting it.
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 Greek hero's ship, its planks replaced one by one, gives its name to a famous puzzle about identity?
Theseus
Theseus: Plutarch says the Athenians kept his ship for centuries, swapping each rotten timber for a sound one, until philosophers argued over whether it was still the same ship.
Q 22On an island where knights always tell the truth and knaves always lie, which statement can no islander make?
I am a knave
'I am a knave' can't be said: a knight would be lying and a knave would be telling the truth. Raymond Smullyan named the two tribes in his 1978 puzzle book What Is the Name of This Book?
Q 23Which mathematician proved that no walk could cross each of Königsberg's seven bridges exactly once?
Leonhard Euler
A cow: the four that hang are her teats and the one that dangles behind is her tail. In a 13th-century Icelandic saga it is among some thirty-seven riddles that King Heidrek solves.
Q 14In the German riddle where Two-legs sits on Three-legs eating One-leg, what is the Four-legs that steals it?
A dog
A dog: Two-legs is a person on a three-legged stool, eating One-leg, a leg of meat. When the dog makes off with it, the stool becomes the weapon that wins it back.
Q 15In the Grimms' tale '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, which move wins two times in three?
Switching doors
Switching doors: your first pick is wrong two times in three, and each time the host, who must reveal a losing door, leaves the car behind the only door left. Sticking wins just one time in three.
Q 17Where did the 'missing' dollar go in the missing dollar riddle about three hotel guests and a bellhop?
Nowhere: the sum is a trick
Nowhere: the sum is a trick. The guests paid $27, which is the $25 in the till plus the bellhop's $2; adding his $2 to the $27 counts it twice, and the $30 is a red herring.
Q 18In the classic wolf, cabbage and third-passenger river puzzle, what does the farmer ferry across first?
The goat
The goat: it is the only passenger that can't be left alone with either of the others. The puzzle is over 1,100 years old, from a problem collection attributed to Alcuin of York.
Q 19At one move a second, about how long would a 64-disk Tower of Hanoi take?
600 billion years
600 billion years: the fastest solution takes 2 to the 64th minus 1 moves, which at one a second is some 585 billion years, roughly 42 times the age of the universe.
Q 20Which French mathematician sold the Tower of Hanoi as 'N. Claus de Siam'?
Édouard Lucas
Édouard Lucas hid in plain sight: 'Claus' is an anagram of 'Lucas', and the full name rearranges to 'Lucas d'Amiens', after the city where he was born.
Leonhard Euler: to prove it he ignored the map and kept only the land masses and the links between them, a move that founded graph theory.
Q 24The Zebra Puzzle is often called whose 'riddle', despite no evidence he wrote it?
Albert Einstein
Albert Einstein: legend says he wrote it as a boy, but the 1962 Life International version has a house where Kools are smoked, a cigarette brand launched in 1933, when he was 54.
Q 25In the 'bridge and torch' puzzle, which move beats the fastest walker escorting everyone?
Pairing the two slowest
Pairing the two slowest: with walkers who take 1, 2, 5 and 8 minutes, the quick pair shuttle the torch so the 5 and the 8 cross together, which takes 15 minutes against 17 for the escort plan.
Q 26Which phrase is often linked to the nine dots puzzle, a favourite of 1970s management trainers?
Thinking outside the box
Thinking outside the box: the nine dots can be joined by four straight lines only if the lines run past the edge of the square the dots seem to form, which is the point the trainers were making.
Q 27The 2015 viral logic puzzle 'Cheryl's Birthday' came from a maths olympiad in which country?
Singapore
Singapore: the puzzle was set for teenagers in the 2015 Singapore and Asian Schools Math Olympiad, but a TV presenter posted it online as a primary-school question and it went round the world.
Q 28Which paradox says an expected-value calculation suggests you should always swap, though the choices are symmetric?
The two envelopes problem
The two envelopes problem: one envelope holds twice the other, so swapping seems to risk half to gain double. The same sum then tells you to swap straight back, and so on for ever.
Q 29Which term did Edward de Bono coin in 1967 for solving problems by unorthodox means?
Lateral thinking
Lateral thinking: de Bono applied it to everything. He once told British Foreign Office officials that Marmite might ease the Arab-Israeli conflict, by supplying zinc that he said a diet of unleavened bread lacks.
Q 30A riddle whose answer turns on a pun, like 'What's black and white and red all over?', is called what?
A conundrum
A conundrum, in the strict sense, is a riddle answered by a play on words: here 'red' is heard as 'read', and the answer is a newspaper.