100 Long Riddles To Solve On Long Winter Evenings

On the first day of school, someone murdered the English teacher. There were four people at the school that the police suspected had done it: the janitor, a history teacher, a basketball coach, and the principal. These were their alibis: The janitor said he was cleaning the bathrooms. The history teacher said he was giving a mid-year test. The basketball coach said he was running practice drills with his players. The principal said he was in his office. After giving their alibies, the police arrested the killer immediately. Who killed the English teacher and how did the police know? 

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? 

Consider this: Arnold Schwarzenegger has a big one. Michael J. Fox has a small one. Prince doesn’t have one. The Pope has one but never uses it. Bill Clinton has one and uses it all the time. What is it?

What does man love more than life, and hate more than death or mortal strife; that which satisfied men want; the poor have, and the rich require; the miser spends, the spendthrift saves, and all men carry to their graves?

Jessica is telling her friends this story and asks them to guess if it’s the truth or a lie: “There was a man sitting in a house at night that had no lights on at all. There was no lamp, no candle, and no other source of light. Yet, he sat in the house and read his book happily.” Her friends say she’s lying, but Jessica corrects them and says she’s telling the truth. Jessica’s story is true — but how? 

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?

Two fathers and their two sons go on a fishing trip together. Each one catches a fish to take home with them. They don’t lose any fish, and yet when they get home they, only have three fish. How is this possible? 

A prisoner is called to be questioned by the guards. The guards tell the prisoner: “If you tell a lie, we will hang you and if you tell the truth, we will shoot you.” What did the prisoner say to save himself? 

I am a fruit, but also a shape. If you had two of me, I would sound just the same. If you rearrange my letters, it could be a crime. Add me to a montage and I can become a different fruit. Remove my head and you can still listen; take away the end and I can still be eaten. Without a piece of the center, I am still a word; take away all of the middle and I am just an acronym. What am I?

I beam, I shine, I sparkle white. I'll brighten the day with a single light. I'll charm and enchant all. I'll bring the best in you all. What am I? 

The captain of a ship told an interesting story. “I have traveled the oceans far and wide. One time, two of my sailors were standing on opposite sides of the ship. One was looking west and the other one east. And at the same time, they could see each other clearly. Can you tell me how that was possible?” 

I am beautiful, up in the sky. I am magical, yet I cannot fly. To people I bring luck, and to some people, riches. The boy at my end does whatever he wishes. What am I? 

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?

Grandpa went for a walk, and it started raining. He forgot to bring an umbrella and didn’t have a hat. When he got home, his clothes were soaking wet, but not a hair on his head was wet. How was this possible?

You walk into a room and see a bed. On the bed, there are two dogs, five cats, a giraffe, six cows, and a goose. There are also three doves flying above the bed. How many legs are on the floor?

One night, a woman receives a call from the police. They tell her that her husband was murdered, and she should come to the crime scene as soon as possible. The woman drops the phone, shocked, and drives 20 minutes to the crime scene. As soon as she reaches the crime scene, the police arrest her and she is convicted of murder. How do the police know she committed the crime?

One day, a magician was boasting about how long he could hold his breath underwater. His record was 6 minutes. A kid that was listening said, “that’s nothing, I can stay underwater for 10 minutes using no equipment or air pockets!” The magician told the kid if he could do that, he’d give him $10,000. The kid did it and won the money. How?

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? 

The person who makes it has no need for it. He who purchases it does not use it. The person who does use it does not know they are. What is it?

Jim and Sarah are in a long-distance relationship. Jim buys an engagement ring for Sarah and wants to mail it to her. Unfortunately, the only way to ensure the ring will be received is to place a lock on the package. Jim has locks and Sarah has locks, but neither has keys for each other’s locks. How can they make sure the ring isn’t stolen?