Riddle: A boy has as many sisters as brothers, but each sister has only half as many sisters as brothers. How many brothers and sisters are there in the family?
Answer: Four brothers and three sisters.
Riddle: Three-fourths of a cross, and a circle complete, An upright where two semicircles meet, A rectangle triangle standing on feet, Two semicircles, and a circle complete. What is it?
Answer: The word Tobacco.
Riddle: There is one word in the English language which is universally considered a preventive of harm; change a certain letter in it, and you make it an act of cruelty. What are the words?
Answer: Prescription—proscription.
Difficult Riddles
Riddle: A 300 ft. train is traveling 300 ft. per minute must travel through a 300 ft. long tunnel. How long will it take the train to travel through the tunnel?
Answer: Two minutes. It takes the front of the train one minute and the rest of the train will take two minutes to clear the tunnel.
Riddle: Tom volunteered to be the chief organizer for the world's tether ball championships. There were 657 contestants from around the world. The tournament was set up whereby the winner would advance and the loser would be eliminated. Since there was an odd number of participants, the initial pairing leaves one player out. That player gets a bye and automatically advances to the next round. How many matches will Tom have to schedule to determine the tether ball champion?
Answer: 656 matches will be needed.
Difficult Riddles
Riddle: Why is an orange not like a church bell?
Answer: Because it is never peeled (pealed) but once.
Riddle: My first may be fashioned of iron or wood,  And at window or door for safety is placed;  In village or town, it does more harm than good, Leading people their health, time, and money to waste. My second's a lady, bewitching and fair, And for love of her people will labor and strive; Will rise before dawn, and be wearied with care, And pursue her with ardor as long as they live. My whole is what ladies admire and approve, The shopkeeper's boast-the purchaser's prize; 'Tis a ninepenny chintz-'tis a one-shilling glove- It is something which makes people open their eyes. What am I?
Answer: Bar-gain.
Difficult Riddles
Riddle: 'Tis found in our troubles, 'tis mixed with our pleasures, 'Tis laid up above with our heavenly treasures; 'Tis whispered in heaven, and 'tis muttered in hell, And it findeth a place in each sybilline spell; In Paradise nestled, 'mid Eden's fair flowers, It has sported with Eve in rose-perfumed bowers; 'Tis muttered in curses, yet breathed in our prayers; From the path of our duty it tempts us in snares. Deep, deep in our hearts you will find it engraved; Though in misery sunk, yet from sin it is saved. 'Tis found in the stream that flows on to the ocean; Though in bustle forever, 'tis ne'er in commotion. 'Tis wafted afar o'er the land in each breath; In the grave 'tis decaying-you'll find it in death. It is floating away on the broad stream of time, Yet it findeth a place in eternity's clime. In the legends of nations it holdeth a place; There's no charm without it to the beautiful face. In thunder you'll hear it, if closely you listen; In moonbeam and sunbeam forever 'twill glisten. In the dew-drop it sparkles; 'tis found in the forest; It whispers in peace when our need is the sorest. What am I?
Answer: The letter E.
Riddle: What are the 2 longest words in the English language that can be typed using only your left hand on the keyboard?
Answer: 1: Stewardesses 2: Reverberated
Riddle: It speaks with a hard tongue, it cannot breathe, for it has no lungs. What is it?
Answer: A Bell.
Riddle: I am not found on any ground, But always in the air; Though charged each cloud with thunder loud, You can not find me there. Now, if from France you choose to dance Your way just into Spain, I there am seen, and near the queen, In hail, in mist, and rain. What am I?
Answer: The letter I.
Riddle: What is the 4 digit number in which the first digit is one-fifth of the last, and the second and third digits are the last digit multiplied by 3?
Answer: 1155.
Riddle: A hundred stones are placed, in a straight line, a yard distant from each other. How many yards must a person walk, who undertakes to pick them up, and place them in a basket stationed one yard from the first stone?
Answer: In solving this question it is clear that to pick up the first stone and put it into the basket, the person must walk two yards, one in going for the stone and another in returning with it; that for the second stone he must walk four yards, and so on increasing by two as far as the hundredth, when he must walk two hundred yards, so that the sum total will be the product of 202 multiplied by 50, or 10,100 yards. If any one does not see why we multiply 202 by 50 in getting the answer, we refer him to his arithmetic.
Riddle: Walking home one day, you take a short cut along the train tracks. The tracks cross a narrow bridge over a deep gorge. At the point you are 3/8 of the way across the bridge, you hear the train whistle somewhere behind you. You charge across the bridge, and jump off the track as the train is about to run you down. As it happens, if you had gone the other way, you would have reached safety just before being run over as well. If you can run ten miles per hour, how fast is the train moving?
Answer: The train is moving at 40 miles per hour. Imagine that a friend is walking with you. When the train whistle blows, you head away from the train, he heads toward it. When he reaches safety, you will be 6/8 (or 3/4)of the way across the bridge, and the train will have just reached the bridge. For the train to cross 4/4 of the bridge in the time you cross the remaining 1/4, the train must be moving four times your speed.
Riddle: Twelve flags stand equidistant along the track at the stadium. The runners start at the first flag. A runner reaches the eighth flag 8 seconds after he starts. If he runs at an even speed, how many seconds does he need altogether to reach the twelfth flag?
Answer: Not 12 seconds. There are 7 segments from the first flag tot the eighth, and 11 from the first to the twelfth. He runs each segment in 8/7 seconds; therefore, 11 segments take 88/7= 12 4/7 seconds.
Riddle: My only timepiece is a wall clock. One day I forgot to wind it and it stopped. I went to visit a friend whos watch is always correct, stayed awhile, and then went home. There I made a simple calculation and set the clock right. How did I do this even though I had no watch on me to tell how long it took me to return from my friend's house?
Answer: Before I left, I wound the wall clock. When I returned, the change in time equaled how long it took to go to my friends house and return, plus the time I spent there. But I knew the latter because I looked at my friends watch when I arrived and left. Subtracting the time of the visit from the time I was absent from my house, and dividing by 2, I obtained the time it took me to return home. I added this time to what my friend watch showed when I left, and set the sum on my wall clock.
Riddle: Granny looked up from her rocking chair and said: As far as I can tell, there is only one anagram of the word trinket. What is it?
Answer: The word knitter.
Riddle: Lazy Larry agreed to work on a job for his brother-in-law for thirty hours at eight dollars an hour, on the condition that he would forfeit ten dollars per hour for every hour that he idled. At the end of the thirty hours Larry wasn't owed any money and didn't owe his brother-in-law any money either. How many hours did Larry work and how many hours did he idle?
Answer: Lazy Larry worked 16-2/3 hours and idled 13-1/3 hours. 16-2/3 hours, at $8.00 an hour amounts to the same amount as 13-1/3 hours at $10.00 per hour.
Riddle: A house has 6 stories, each the same height. How many times as long is the ascent to the sixth floor as the ascent to the third?
Answer: 2 1/2 times (5/2, not 6/3).
Riddle: A man had a bar of lead that weighed 40 lbs., and he divided it into four pieces in such a way as to allow him to weigh any number of pounds from one to forty. What are the weights of the four pieces?
Answer: 1, 3, 9, 27, are the weights of the four pieces.