These riddles come from a Halloween Party book from 1912. The idea behind them was to tell riddles to kids towards the end of the party when they’re all tired. I took out all of the ones that were outdated. I tried to update some of the language of the other riddles to make them more modern. Hope you enjoy them with kids you know!

RIDDLES

Why are sleepy people like wheels? Answer: Because they are tired.

Why does a duck go into the water?–Answer: For divers reasons.

Spell “blind pig” in two letters? P G; a pig without an I.

Which bird can lift the heaviest weights?–The crane.

Why is a wise man like a pin?–He has a head and comes to a point.

Why may carpenters reasonably believe there is no such thing as
stone?–Because they never saw it.

What is that which is put on the table and cut, but never eaten?–A
pack of cards.

Why does a sculptor die horribly?–Because he makes faces and busts.

What lives upon its own substance and dies when it has devoured
itself?–A candle.

What thing is it that is lower with a head than without one?–A
pillow.

If all the seas were dried up, what would everybody say?–We haven’t a
notion (an ocean).

Why is a fishmonger never generous?–Because his business makes him
sell fish (selfish).

What is that from which you may take away the whole and yet there will
be some remaining?–The word wholesome.

Why is a vine like a soldier?–Because it is listed and has ten drills
(ten-drils) and shoots.

Why is an opera-singer like a confectioner?–Because she deals in ice-
creams (high screams).

What belongs to you, but is used more by your friends than by
you?–Your name.

Why is a spider a good correspondent?–Because he drops a line at
every post.

When is the clock on the stairs dangerous?–When it runs down.

Why is the letter “k” like a pig’s tail?–Because it comes at the end
of pork.

What is the keynote to good manners?–B natural.

When has a man four hands?–When he doubles his fists.

What trees has fire no effect upon?–Ashtrees; because when they are
burned, they are ashes still.

What is the difference between a teacher and an engine-driver?–
One minds the train and the other trains the mind.

A man had twenty sick (six) sheep, and one died; how many were left?–
19.

What is that which everybody has seen but will never see again?–
Yesterday.

Which is the best day for making a pancake?–Friday.

Which is the smallest bridge in the world?–The bridge of your nose.

What four letters would frighten a thief?–O I C U.

What is that which goes from London to York without moving?–The road.

When may a chair be said to dislike you?–When it can’t bear you.

Why is B like a hot fire?–Because it makes oil Boil.

Why was the first day of Adam’s life the longest?–Because it had no
Eve.

Why is a washerwoman like a navigator?–Because she spreads her
sheets, crosses the line, and goes from pole to pole.

Why is an author the queerest animal in the world?–Because his tale
comes out of his head.

Why is it that a tailor won’t attend to business?–Because he is
always cutting out.

When are we all artists?–When we draw a long face.

When is a tradesman always above his business?–When he lives over his
shop.

What ships hardly ever sail out of sight?–Hardships.

When is an artist a dangerous person?–When his designs are bad.

What motive led to the invention of railroads?–The locomotive.

Why are deaf people like Dutch cheeses?–Because you can’t make them
here.

Who was the first whistler?–The wind.
What tune did he whistle?–Over the hills and far away. (This line is from Tom Tom the Piper’s Son.)

Why need a traveler never starve in the desert?–Because of the sand
which is (sandwiches) there.

Why is a little man like a good book?–Because he is often looked
over.

Why is a pig in a parlor like a house on fire?–Because the sooner it
is put out the better.

Spell “enemy” in three letters?–F O E.

Which is the only way that a leopard can change his spots?–By going
from one spot to another.

Why did Eve never fear the measles?–Because she’d Adam.

When is a tall man a little short?–When he hasn’t got quite enough
cash.

What houses are the easiest to break into?–The houses of bald people;
because their locks are few.

Why is a watch the most difficult thing to steal?–Because it must be
taken off its guard.

What plant stands for No. 4?–IV.

How can a gardener become thrifty?–By making the most of his thyme,
and by always putting some celery (salary) in the bank.

Why is it probable that beer was made in the Ark?–Because the
kangaroo went in with hops, and the bear was always bruin.

“What was the biggest thing you saw at the World’s Fair?” asked a wife
of her husband.–“My hotel bill!” said he.

Why is C like a schoolmistress?–Because it forms lasses into classes.

What is that which never asks any questions and yet requires many
answers?–The street-door (the front door).

Which is the longest word in the English language?–Smiles; because
there is a mile between the first and last letters.

Which is the oldest tree in England?–The Elder Tree.

What is that which happens twice in a moment and not once in a
thousand years?–The letter M.

If you’re interested, you can read the whole book that these riddles are from. It’s online at: Games for Hallow-e’en.