Difficult Riddles
Riddle: To form me, time is the foundation, it's difficult to break me from the outside, but I'll break as long as you touch from the inside. What am I?
Answer: Trust.
Riddle: How high would you have to count before you would use the letter A in the English language spelling of a whole number?
Answer: One thousand.
Riddle: Whether the weather is hot or cold, I will take you wherever you need to go. The direction you take will determine the place. There may be the most difficult roads, but they often lead to the most beautiful destinations. What am I?
Answer: A journey.
Riddle: Sometimes I am loud and viewed with distaste. Poke out my eye, then I'm on the front of your face. What am I?
Answer: A noise, remove the "eye" aka "i" and you get a nose.
Riddle: General Gasslefield, accused of high treason, is sentenced to death by court-martial. He is allowed to make a final statement, after which he will be shot if the statement is false or will be hung if the statement is true. Gasslefield makes his final statement and is released. The Question: What could he have said?
Answer: General Gasslefield said: "I will be shot." If this statement was true, he would have been hung and thus not be shot. But then his statement would be false, which implies that he should be shot, making the statement true again, etc... In other words: the verdict of the court-martial could not be executed and the general was released.
Riddle: Dynamite is a tool that can be used to cut down trees. Cutting a tree 18 inches in diameter requires five sticks of dynamite: one on the north, south, east and west sides of the tree, and the fifth stick on the side to which the tree should fall. During the construction of a dam, a tree 18 inches in diameter was completely covered by water. Since the treetop was fouling the boat's propellers, it had to be cut down. A diver went down and put a stick of dynamite on the four sides of the tree. Since the current is flowing south at 2 knots per hour, on which side of the tree would you instruct the diver to put the fifth stick of dynamite if you wanted the tree to fall north?
Answer: It doesn't matter where the fifth stick is placed, since the tree won't fall in any direction. Being wood, it will float and rise to the surface.
Riddle: I run, it runs, I stop, it runs. What it it?
Answer: My watch.
Riddle: I bubble and laugh And spit water in your face. I am no lady, And I don't wear lace. What am I?
Answer: A fountain.
Riddle: Shirley's two-year-old granddaughter carries around with her something Shirley recently purchased for her in the produce section of a local supermarket. The little girl has the item wrapped in a blanket, pretending it is her baby. She carries her "baby" with her everywhere she goes, and even sleeps with it at nighttime. However, the "baby" has no body, but consists of a brown head with two eyes and a mouth; or is it two eyes and a nose? Sometimes it is difficult to tell, but only the face of the baby peeks out from the surrounding blanket. What type of produce is this "baby" that Shirley's granddaughter carries around with her?
Answer: The two-year-old’s “baby” is actually a coconut which she wraps in a blanket, with the three circular indentations of the “face” turned outward.
Riddle: Part pickle, part crazy, You can't call this flower lazy. It perks its head up with a snout And if it had a voice - I'm sure it'd shout. What is it?
Answer: A Daffodil.
Riddle: Deep, deep, do they go. Spreading out as they go. Never needing any air. They are sometimes as fine as hair. What are they?
Answer: Roots.
Riddle: During WWII, there was a bridge connecting Germany and Switzerland, and on the German side, there was a sentry tower with a guard in it. He would come out every three minutes to check on the bridge, and he had orders to turn back anyone who tried to get into Germany, and shoot anyone trying to escape without a pass. There was a woman who desperately needed to get into Switzerland, and she knew she didn't have time to get a pass. It would take her at least six minutes to cross the bridge, but she managed to do it. How?
Answer: When the sentry went into the tower, she would start to cross into Switzerland, and when he came out, she would start to walk back into Germany. When he saw her, he would tell her to turn back into Switzerland.
Riddle: With lines and scars, I feel the sun but see no stars. I'm shed, I'm stretched, I hide what's within. What am I?
Answer: Skin. The skin is our body’s remarkable outer shield. It carries the story of our lives in the form of lines and scars, sensing the warmth of the sun or the chill of the air—yet it cannot see. Always renewing itself as old cells are shed, skin stretches to accommodate growth, pregnancy, and movement. At the same time, it serves as a protective veil, concealing the intricate organs and tissues beneath. All these clues point unmistakably to the skin: the living canvas that both reveals and hides who we are.
Riddle: A man is in a room and the door is locked so he can't get out. He has with him a piano, a calendar, and a bed. How does he eat, drink, and get out?
Answer: He uses the dates from the calendar to eat, the springs from the bed to drink and the keys from the piano to get out.
Riddle: When the day after tomorrow is yesterday, today will be as far from Wednesday as today was from Wednesday when the day before yesterday was tomorrow. What is the day after this day?
Answer: The day is Thursday!
Riddle: There were two scientists who were looking through the woods. They found two people on the ground who where dead. They examined the two people and said they were the first people on earth.  How did they know?
Answer: The two people didn't have belly buttons.
Riddle: Dawns away, The day's turned grey And I must travel far away. But I'll be back And then we'll track, The light of yet another day. What is it?
Answer: The Sun or a shadow. The riddle is written as if the sun is speaking to us. It's not saying the sun tracks its light; it's saying:
  • “I’ll be back” → the sun will rise again.
  • “And then we’ll track the light”we(humans) will follow, notice, and live by its light through another day.
  the sun leaves (sets), returns (rises), and then together with us it “tracks” the day—meaning we move through the day guided by its light. If you don’t like that reading, a more literal alternative answer that fits the “tracking light” idea nicely is a shadow  
Riddle: You have a painting with a string attached to it. The string is attached to the upper two corners of the painting. In the wall there are two nails, horizontally next to each other. The string must be hung on the nails in such a way that the painting falls down if any of the two nails is pulled out of the wall. The painting must hang under the nails and must hang on the string. The Question: How must the painting be hung?
Answer: To solve this, loop the string around each nail twice in a criss-cross pattern, ensuring it hangs below the nails. First, loop the string around the left nail, then the right nail, then back to the left, and finally to the right, and attach the ends to the painting. This creates a configuration where each nail has two sections of string supporting it, but removing one nail will cause all the tension to shift, causing the painting to fall. 
Riddle: A grandfather clock chimes the appropriate number of times to indicate the hour, as well as chiming once at each quarter hour. If you were in another room and heard the clock chime just once, what would be the longest period of time you would have to wait in order to be certain of the correct time?
Answer: You would have to wait 90 minutes between 12:15 and 1:45. Once you had heard seven single chimes, you would know that the next chime would be two chimes for 2 o'clock.
Riddle: Since a person uses about the same amount of energy walking 2 miles as they would run for 2 miles, would a person use more energy running for 10 minutes, walking for ten minutes, or the same amount of energy?
Answer: Since a person running for 10 minutes would cover more distance than that same person would walking for 10 minutes, he would use more energy running for 10 minutes.