Charlotte Foster

Retirement Life

10 long riddles to give your brain a workout

10 long riddles to give your brain a workout

Who doesn’t love a good riddle? Whether you prefer easy riddles, hard riddles, or short riddles, there’s just something about trying to solve these brain busters that keeps us coming back for more. Come on, is there anything better than finally solving a mind-bender we’ve been stuck on for a while?

You may consider yourself a master of riddles, but remember – you haven’t seen our list of long riddles yet. Buckle up – these riddles will get your gears turning!

Can you solve these long riddles?

The farmer's river crossing

A farmer went to a market and bought a wolf, a goat, and a cabbage. On his way home, the farmer came to the bank of a river and rented a boat. But crossing the river by boat, the farmer could carry only himself and a single one of his purchases: the wolf, the goat, or the cabbage. If left unattended together, the wolf would eat the goat, or the goat would eat the cabbage. The farmer’s challenge was to carry himself and his purchases to the far bank of the river, leaving each purchase intact. How did he do it?

Answer: The farmer takes seven trips over – here are his steps:

Take the goat over


Take the wolf or cabbage over

Return with the goat

Take the cabbage or wolf over


Take goat over

Note: The riddle doesn’t forbid the farmer from bringing a purchase back, which makes the steps above possible.

The suspicious hotel visit

A woman is sitting in her hotel room and hears a knock at the door. She opens the door to see a man whom she’s never met before. He says, “I’m sorry, I have made a mistake, I thought this was my room.” He then goes down the corridor and into the elevator. The woman goes back into her room and calls security. What made the woman so suspicious of the man?

Answer: If he really thought it was his hotel room, he would have tried to open the door – not knock on it first.

Man and a brick

A man is found unconscious in front of a store at two in the morning. His head is bleeding and there’s a brick laying next to him. When the police arrive, they carry the man to jail. Why did they arrest him?

Answer: The man was trying to rob the store. He threw a brick at the store’s bullet-proof window and it bounced back and hit him.

My three sons

A father told his three sons he would die soon and he needed to decide which one of them to give his property to. He said, “Go to the market and buy something that is large enough to fill my bedroom, but small enough to fit in your pocket. From this, I will decide which of you is the wisest and worthy enough to inherit my land.” They all went to the market, and each came back with a different item. The father told his sons to come into his bedroom one at a time and try to fill up his bedroom with their item. The first son came in and put some pieces of cloth he bought and laid them across the room, but it barely covered the floor. The second son came in and laid some hay on the floor, but there was only enough to cover half the floor. The third son came in and showed his father what he bought. He wound up getting the property. What did the third son show his father?

Answer: A box of matches. Whenever he lit a match, it filled the room with light.

The big family

There’s a girl who has a large family. She has an equal amount of brothers and sisters, but each brother only has half as many brothers and sisters. What’s the correct amount of brothers and sisters?

Answer: Four sisters and three brothers.

Door to paradise

You stand in front of two doors. A guard stands next to each door. You know the following things: one path leads to paradise, the other leads to death. You cannot distinguish between the two doors. You also know that one of the two guards always tells the truth and the other always lies. You have permission to ask one guard one question to discover which door leads to paradise. What one question would you ask to guarantee you enter the door to paradise?

Answer: Ask, “Which door would the other guard say leads to paradise?”

The basket full of hats

There is a basket full of hats. Three are white and two are black. Three men, Tom, Tim and Jim, each take a hat out of the basket and put it on their heads without seeing the hat they selected or the hats the other men selected. The men arrange themselves so Tom can see Tim and Jim’s hats, Tim can see Jim’s hat, and Jim can’t see anyone’s hat. Tom is asked what colour his hat is and he says he doesn’t know. Tim is asked the same question, and he also doesn’t know. Finally, Jim is asked the question, and he does know. What colour is his hat?

Answer: The hat is white. If Tom doesn’t know his hat colour then the other two men’s hats cannot be both black otherwise he would know his hat is white. When Tim doesn’t know his hat colour either, that means Jim’s hat could not be black otherwise Tim would have to know his hat was white based on Tom’s answer.

What word am I?

Consider this about a word: The first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?

Answer: Heroine.

The lake house

Sally lives in a place where six months of the year is mild summer and the temperature drops significantly the other six months. She owns a lake where there is a small island. She wants to build a house on the island and needs to get materials there. She doesn’t have a boat, plane, or anything to transport them to the island. How does Sally solve this problem?

Answer: She waits to take the materials over during the colder months because the lake will freeze over, so she can walk over it.

The old horror house

You walk into an old horror house. It has no power or plumbing. Once inside, you see three doors. Each door has a number on it. Behind each door is a way for you to die. Behind door number one, you die by getting eaten by a lion. Behind door number two, you die by getting murdered. Behind door number three, you die by electric chair. You can’t turn back, so you have to go through a door. Which door do you go through?

Answer: Door number three – the house has no power, which means it doesn’t have electricity. Therefore, the electric chair won’t work.

Image credit: Getty Images

This article first appeared on Reader's Digest.