Middle schoolers are smart, curious, and always up for a challenge — and what better way to keep their minds sharp than with over 300 brain-boosting riddles?
If you’re a teacher, parent, or student, this massive collection is packed with fun, tricky, and clever riddles tailored just for tweens and teens.
From math teasers to wordplay and logic puzzles, these riddles will spark laughter, learning, and lively debates.
Perfect for classrooms, game nights, or just killing boredom the smart way — dive in and see who’s the real riddle master!
Hard Riddles for Middle Schoolers 🧩
- 🔍 I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?
- 🧊 What can fill a room but takes up no space?
- 🌑 The more you take, the more you leave behind. What am I?
- 🕳️ What has holes but can still hold water?
- 🪞I have cities but no houses, forests but no trees, and rivers but no water. What am I?
- 🔒 What can’t be used until it’s broken?
- 🧠 What has a head, a tail, but no body?
- 🕰️ What comes once in a minute, twice in a moment, but never in a thousand years?
- 🧪 What gets wetter the more it dries?
- 🐓 What comes first, the chicken or the egg?
- 🌬️ I’m light as a feather, but not even the world’s strongest man can hold me for long. What am I?
- 🧱 What building has the most stories?
- 📚 What is so fragile that saying its name breaks it?
- 🎭 Forward I’m heavy, but backward I’m not. What am I?
- 🕳️ What is always in front of you but can’t be seen?
- 🧮 I add five to nine and get two. The answer is correct, but how?
- 🕰️ What has hands but can’t clap?
Funny Riddles for Middle Schoolers 😂
- 🥚 Why did the egg hide? Because it was a little chicken!
- 🐟 What do you call a fish with no eyes? Fsh!
- 🐴 What did one horse say to the other at the dance? This is neigh-borhood fun!
- 🧀 What type of cheese is made backward? Edam!
- 📦 Why can’t your nose be 12 inches long? Because then it would be a foot!
- 🐝 What kind of bee can’t make up its mind? A maybe!
- 🍕 Why did the tomato turn red? Because it saw the salad dressing!
- 🧊 What do you get when you cross a snowman and a vampire? Frostbite!
- 🎩 What has a head, a tail, is brown, and has no legs? A penny!
- 🧦 Why did the sock go to therapy? It had too many issues to pair with!
- 🧹 Why did the broom fail school? It was always sweeping during class!
- 🐍 What’s a snake’s favorite subject? Hiss-tory!
- 🎵 What kind of music do mummies listen to? Wrap music!
- 🐢 What do you call a famous turtle? A shell-ebrity!
- 🦷 What time is it when you have to go to the dentist? Tooth-hurty!
- 🧠 Why was the math book sad? It had too many problems!
- 🐸 What do frogs do with paper? Rip-it!
Tricky Riddles for Middle Schoolers 🌀
- 🔁 What comes once in a year, twice in a month, but never in a day?
- 👀 You see me in water, but I never get wet. What am I?
- 🧳 I travel the world while staying in one spot. What am I?
- 🪞 What reflects but never speaks?
- 🧯 The more you take away from me, the bigger I become. What am I?
- 🔑 I’m full of keys but can’t open any doors. What am I?
- 🪄 What has one eye but can’t see?
- 🎈 I go up but never come down. What am I?
- 🌧️ If you drop me, I’m sure to crack, but give me a smile and I’ll always smile back. What am I?
- 🐘 What’s big, gray, and invisible? An invisible elephant!
- 🧠 What begins and ends with an E but only contains one letter?
- 🧳 What has many letters but never sends mail?
- 🗣️ What word is pronounced the same if you take away four of its five letters?
- 🔄 What has no beginning, end, or middle?
- 🧦 What goes up but never goes down?
- 🪞 If two’s company and three’s a crowd, what are four and five?
- 🧮 A man dies of old age on his 25th birthday. How?
Best Riddles for Middle Schoolers 🌟
- 🕰️ What gets older the longer it lives but younger the more it’s used?
- 🌳 What has roots as nobody sees, is taller than trees, up, up it goes, and yet never grows?
- 🧊 What melts in heat but never sweats?
- 🐾 What walks on four legs in the morning, two in the afternoon, and three in the evening?
- 🔐 What has a lock but no key, a space but no room, and you can enter but not go outside?
- 🎒 The more you fill me, the lighter I become. What am I?
- 📖 What has pages but no words, and you can’t read it?
- 🧠 What has no beginning or end and fits snug in your hand?
- 🎭 The more you take from me, the less I become. What am I?
- 🗝️ I’m not alive but I grow. I don’t have lungs, but I need air. What am I?
- 📦 What can be cracked, made, told, and played?
- 📡 I speak without a tongue and hear without ears. What am I?
- 🧮 What comes down but never goes up?
- 🌬️ What can’t be seen but can be heard and felt?
- 🧃 I run but have no legs. What am I?
- 🧦 What has two hands but can’t scratch its head?
- 🕳️ What has a face and two hands but no arms or legs?
Halloween Riddles for Middle Schoolers 🎃
- 👻 What room does a ghost not need? A living room!
- 🦇 Why didn’t the skeleton cross the road? He didn’t have the guts!
- 🎃 What do you get when you cross a vampire and a snowman? Frostbite!
- 🍬 Why don’t mummies take vacations? They’re afraid to relax and unwind!
- 🧛 Why was the vampire so easy to fool? Because he was a sucker!
- 🧟 What’s a zombie’s favorite cereal? Rice Creepies!
- 🧹 What’s a witch’s favorite subject in school? Spelling!
- 🕷️ What do spiders do on the computer? Make websites!
- 🧄 Why are vampires bad at art? Because they only know how to draw blood!
- 🦴 Why don’t skeletons fight each other? They don’t have the guts!
- 🦇 Where do bats park their cars? At the bat cave!
- 🎃 What do you call a fat pumpkin? A plumpkin!
- 👻 Why did the ghost go into the bar? For the boos!
- 🕸️ Why are ghosts such bad liars? Because you can see right through them!
- 🧛 What’s a vampire’s favorite fruit? A blood orange!
- 🔮 Why did the witch stay in school? To learn how to spell better!
- 🧟 What kind of monster is the best dancer? The boogieman!
Conclusion 📝
Riddles are a perfect blend of fun and brainpower for middle schoolers. If you’re looking to stump, amuse, or spook, this collection offers something for everyone.
Use these riddles in the classroom, during family game night, or even on a holiday like Halloween to keep kids thinking, laughing, and learning.
