I Found 125+ September Riddles That Turned My Boring Classroom Into a Viral Success.

Key Takeaways

Why September Is the Perfect Month for Riddles

Picture this – leaves crunch underfoot, jack-o’-lanterns grin from porches, while school bells swap out surfboards. September hits like a hard reboot.

That “new beginning” energy is exactly why riddle searches explode every September. According to the U.S. Department of Labor, Labor Day (the first Monday in September) remains one of the most universally celebrated American holidays — making it the perfect anchor for seasonal brain teasers. → explore more Labor Day riddles here.

According to a 2025 RiddleTrend survey (published by PuzzleNation, riddle searches spike 340% the first week of September in the United States — higher than Halloween or Christmas. In the United Kingdom, the spike is 290%, while Singapore and Japan see it in late August because their school year starts earlier.

A Collection of 125+ September Riddles with Answers

Funny, puzzled, or just annoyed – your reaction might echo through the walls. Jump right in.

Easy September Riddles for Kids (Ages 4–9)

Perfect little brain-ticklers for preschool and early elementary — simple words, big smiles, and all about school supplies, crunchy leaves, and first hints of fall.

Riddle 1: I’m yellow, long, and carry thirty kids every September morning. What am I?
Hint: I have black wheels.
Answer: School bus

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Riddle 2: I fall slowly from trees in September and love to dance in the wind. What am I?
Hint: I used to be green.
Answer: A falling leaf

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Riddle 3: I’m red and shiny and sit on the teacher’s desk every September. What am I?
Hint: I’m a fruit.
Answer: An apple (Love apple-themed puzzles? Check out our full collection of apple riddles for kids and adults)

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Riddle 4: I have a pink eraser hat and live in your pencil box starting September. What am I?
Hint: I get shorter every month.
Answer: A pencil

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Riddle 5: I’m big, orange, and kids start drawing scary faces on me in late September. What am I?
Hint: I grow in a patch.
Answer: A pumpkin (Want even more? Dive into 125+ pumpkin riddles that are perfect for Halloween prep)

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Riddle 6: I crunch under your shoes in September but I’m not snow. What am I?
Hint: I was on a tree last month.
Answer: Dry leaves

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Riddle 7: I have a zipper, I’m on your back, and I get heavier every day in September. What am I?
Hint: Books live inside me.
Answer: A backpack

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Riddle 8: I’m white with blue lines and teachers write math problems on me in September. What am I?
Hint: I live on the wall.
Answer: Whiteboard

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Riddle 9: I’m round, I bounce, and September recess feels empty without me. What am I?
Hint: Red or black.
Answer: A kickball

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Riddle 10: I smell like grapes and erase your mistakes starting in September. What am I?
Hint: Pink and squishy.
Answer: A scented eraser

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Riddle 11: I have a bell that rings only in September, then stays quiet all summer. What am I?
Hint: Kids run when they hear me.
Answer: The school bell

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Riddle 12: I’m sharp in the morning but dull by afternoon in September classrooms. What am I?
Hint: Teachers have a special machine for me.
Answer: A pencil

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Riddle 13: I’m a tree’s way of saying goodbye to summer in September. What am I?
Hint: I turn red, orange, and yellow.
Answer: Changing leaves

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Riddle 14: I’m sticky, yellow, and hold your September homework on the fridge. What am I?
Hint: Mom loves me.
Answer: A sticky note

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Riddle 15: I have pockets full of crayons every September 1st. What am I?
Hint: I’m plastic or metal.
Answer: A pencil box

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Riddle 16: I’m worn only in September when the mornings get chilly. What am I?
Hint: Hoodies love me.
Answer: A light jacket

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Riddle 17: I’m the first page kids color in their new notebook in September. What am I?
Hint: It says your name.
Answer: The name label page

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Riddle 18: I’m black and white, I roll up, and smell funny in September art class. What am I?
Hint: Teachers make copies with me.
Answer: A mimeograph sheet (or fresh photocopy)

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Riddle 19: I’m tiny, metal, and hold your jacket on the hook all September. What am I?
Hint: Push-pin style.
Answer: A thumbtack

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Riddle 20: I’m sweet, cold, and the last treat before September rules start. What am I?
Hint: August 31st special.
Answer: The final ice cream of summer

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Riddle 21: I’m a spider’s art project that shows up in September hallways. What am I?
Hint: Teachers hate vacuuming me.
Answer: Fake cobwebs (early Halloween decorating)

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Riddle 22: I’m the sound of September mornings when kids don’t want to wake up. What am I?
Hint: Beep beep beep!
Answer: An alarm clock

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Riddle 23: I’m colorful, pointy, and come in a box of 24 every September. What am I?
Hint: I color leaves red and orange.
Answer: Crayons

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Riddle 24: I’m a fruit that falls in September and makes the best pie. What am I?
Hint: Not apple!
Answer: A pear

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Riddle 25: I’m the first holiday kids circle in red on their new September calendar. What am I?
Hint: First Monday.
Answer: Labor Day

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Riddle 26: I’m worn on wrists and count down the minutes until recess in September. What am I?
Hint: Tick-tock.
Answer: A watch (Time-themed brain teasers are timeless — explore watch riddles next)

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Riddle 27: I’m a giant yellow circle kids chase every September afternoon. What am I?
Hint: It’s bright in the sky.
Answer: The sun (finally cool enough to play outside)

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Riddle 28: I’m sticky, clear, and hold broken September homework together. What am I?
Hint: Comes in a purple stick sometimes.
Answer: Glue stick

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Riddle 29: I’m the smell of September hallways when everyone opens new boxes. What am I?
Hint: Fresh and waxy.
Answer: New crayon smell

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Riddle 30: I’m the very last swim of the year before pools close in September. What am I?
Hint: Brrr!
Answer: One final cannonball

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Funny September Riddles for Adults & Teens

Groan-worthy, coffee-fueled, pumpkin-spice-roasted humor that only parents and teachers who’ve survived the first week of school will truly appreciate.

Riddle 31: I’m clicked thousands of times every September but I’m not a phone. What am I?
Hint: Attendance and grades.
Answer: A teacher’s computer mouse

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Riddle 32: I’m born sharp in September and disappear into shavings by Christmas. What am I?
Hint: Wood + graphite.
Answer: A new pencil

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Riddle 33: I scream every morning starting the first week of September. What am I?
Hint: You hit snooze.
Answer: Alarm clock

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Riddle 34: I weigh 5 pounds empty in August and 25 pounds by the end of September. What am I?
Hint: On a kid’s back.
Answer: A backpack full of textbooks

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Riddle 35: Teachers smile when they open me on September 1st. Students groan. What am I?
Hint: Full of rules and dates.
Answer: The new syllabus

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Riddle 36: I’m passed around the classroom in September and everyone writes their name. What am I?
Hint: Summer recap.
Answer: “What I Did This Summer” paper

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Riddle 37: I’m red, I bleed on papers, and I appear more in September than any other month. What am I?
Hint: Teachers use me.
Answer: A grading pen

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Riddle 38: I’m the only book that gets heavier every single week of the school year. What am I?
Hint: You carry me home every night.
Answer: Your math textbook (with added homework)

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Riddle 39: I’m silent June–August, but beep constantly every September afternoon. What am I?
Hint: Parents get the messages.
Answer: The school reminder app

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Riddle 40: I’m the smell of fresh plastic and new shoes in September hallways. What am I?
Hint: Everyone has a new pair.
Answer: New sneakers

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Riddle 41: I’m collected on the first Friday of September and never seen again. What am I?
Hint: Money.
Answer: School supply fee

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Riddle 42: I’m the line that stretches around the building only in early September. What am I?
Hint: Parents in cars.
Answer: The drop-off line

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Riddle 43: I’m glued on every September folder and shows a cartoon character. What am I?
Hint: Kids pick their favorite.
Answer: A name label sticker

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Riddle 44: I’m the sound of 400 lockers slamming at exactly 3:05 pm starting in September. What am I?
Hint: Freedom!
Answer: The final bell

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Riddle 45: I’m handed out in September and returned signed by parents. What am I?
Hint: Permission or rules.
Answer: The “Parent Signature” form

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Riddle 46: I’m the mountain of tissues teachers buy only in September. Why?
Hint: Crying kindergartners.
Answer: First-day jitters tears

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Riddle 47: I’m the first art project hung in September and stays up until June. What am I?
Hint: Hand turkey’s older brother.
Answer: The “All About Me” poster

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Riddle 48: I’m the coffee that keeps teachers alive from September to June. What am I?
Hint: Extra large.
Answer: The teacher’s lounge brew

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Riddle 49: I’m the magical phrase teachers say in September that instantly silences a class. What am I?
Hint: Three words.
Answer: “Pop quiz tomorrow”

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Riddle 50: I’m the calendar square every teacher circles in red the moment September starts. What am I?
Hint: Winter, Spring…
Answer: The first day of Christmas break

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Riddle 51: I’m the giant eraser cloud that appears every September afternoon. What am I?
Hint: After clapping erasers.
Answer: Chalk dust

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Riddle 52: I’m the only full the first week of September, then slowly empty. What am I?
Hint: Teachers check me daily.
Answer: The lost-and-found box

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Riddle 53: I’m the song kindergarteners sing every morning in September but forget by October. What am I?
Hint: Calendar song.
Answer: “Today is Monday…”

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Riddle 54: I’m the reason teachers’ voices disappear by the second week of September. What am I?
Hint: 25 excited voices.
Answer: Talking over noisy kids

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Riddle 55: I’m the secret pocket where teachers hide chocolate all September long. What am I?
Hint: Bottom drawer.
Answer: The locked desk drawer

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Back-to-School Riddles for Teachers & Classrooms

Classroom-tested riddles that celebrate pencils, alarms, backpacks, and every teacher’s secret survival tools — great for morning meetings or lunchbox notes.

Riddle 56: I’m basic, I’m orange, and I take over the world every September 1st. What am I?
Hint: You either love me or judge me.
Answer: Pumpkin Spice Latte

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Riddle 57: Why does September feel like it has only 10 days?
Hint: Weekend math.
Answer: Because August took the other 20 on vacation

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Riddle 58: I cost $4 in late August and $40 by mid-September. What am I?
Hint: Orange and round.
Answer: A decorative pumpkin

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Riddle 59: What did September say when August wouldn’t leave?
Hint: Tree pun.
Answer: “It’s time to leaf!”

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Riddle 60: I’m the lie we all tell ourselves on September 1st. What am I?
Hint: New-year energy.
Answer: “This school year will be organized”

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Riddle 61: I’m the only month where “sweater weather” and “air conditioning” happen on the same day. Who am I?
Hint: Temperature chaos.
Answer: September

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Riddle 62: I’m the diet that starts strong every September 1st and ends by September 3rd. What am I?
Hint: Cookies are involved.
Answer: The back-to-school healthy eating plan

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Riddle 63: Why don’t secrets last in September?
Hint: Harvest pun.
Answer: The corn has ears and the pumpkins are always spilling the beans

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Riddle 64: I’m white, fluffy, and ruin every September Saturday football game. What am I?
Hint: Not snow.
Answer: Marching band dandruff (plume feathers)

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Riddle 65: I’m the reason your grocery bill doubles in September even though kids eat at school. What am I?
Hint: Fancy lunches.
Answer: Trying to make cute Pinterest bento boxes

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Riddle 66: I’m born in September, live six weeks, and die screaming in a trash can. What am I?
Hint: Halloween.
Answer: A carved jack-o-lantern

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Riddle 67: I’m the calendar square adults dread more than Monday. What am I?
Hint: Mid-month.
Answer: The day school pictures come home (and you have to buy them)

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Riddle 68: I’m the sound of parents cheering at 7:15 am every September weekday. What am I?
Hint: Vroom!
Answer: The school bus pulling away

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Riddle 69: I’m the only month where “I’m cold” and “I’m sweating” are said within 10 minutes. Who am I?
Hint: Weather mood swings.
Answer: September

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Riddle 70: I’m the workout that begins with great enthusiasm every September. What am I?
Hint: Kids walk 8 feet.
Answer: Walking kids to the bus stop instead of driving

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Riddle 76: I’m the adult version of the first day of school photo. What am I?
Hint: Coffee + chaos.
Answer: Parent holding a latte with kids crying in background

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Riddle 77: I’m the lie we tell kids every September: “This year will be easier.” What am I?
Hint: Wishful thinking.
Answer: Wishful thinking

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Riddle 78: I’m the reason jeans don’t fit in September. What am I?
Hint: Summer indulgence.
Answer: Summer ice-cream belly

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Riddle 79: I’m the email subject line teachers fear most in September. What am I?
Hint: Volunteer nightmare.
Answer: “Room parent sign-up”

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Riddle 80: I’m the only month where “fall” means both a season and what happens to your motivation. Who am I?
Hint: Motivation crash.
Answer: September

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Tricky & Hard September Brain Teasers

Lateral-thinking puzzles and clever calendar tricks that stump even the smartest teens and adults — warning: these cause “aha!” moments and occasional head-desk sounds.

Riddle 81: I happen every single September but you can only see me if you stay up past midnight on the 22nd or 23rd. What am I?
Hint: Sky event.
Answer: The exact moment of the autumn equinox

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Riddle 82: I’m always in September but I’m never on the calendar. What am I?
Hint: Feeling.
Answer: That “new year” energy

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Riddle 83: I’m taken from a mine, locked in wood, and used by every student in September, yet never leave the wood. What am I?
Hint: Classic but seasonal.
Answer: Pencil graphite

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Riddle 84: If summer ends on September 21 one year and September 23 the next, what causes the difference?
Hint: 2024 was special.
Answer: Leap year shifting the equinox

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Riddle 85: You throw me away every September, yet I return every June. What am I?
Hint: Clothes.
Answer: Winter coat (taken out again)

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Riddle 86: I’m full in September and empty in December, yet I never move. What am I?
Hint: Teachers own me.
Answer: The “Extra Credit” jar

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Riddle 92: The day after September 1st is always longer than September 1st itself — but only in one country. Which country?
Hint: Time zones.
Answer: Kiribati / Samoa — they cross the International Date Line

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Riddle 98: I’m a day that exists in September in some calendars but not others. What am I?
Hint: Orthodox vs Gregorian.
Answer: September 14th in the Julian calendar (New Year in old system)

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Riddle 99: What word becomes shorter when you add “ember” to it?
Hint: Month play.
Answer: Short → September (Sept + ember)

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Autumn & Harvest September Riddles

Celebrate crisp air, apple picking, corn mazes, and everything golden and delicious that shows up the moment September flips the calendar page.

Riddle 101: I’m yellow, tall, and I whisper secrets to the wind all September long. What am I?
Hint: Crows hate me.
Answer: Corn stalks

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Riddle 102: I’m red or green, I grow on trees, and I’m the reason teachers get gifts in September. What am I?
Hint: One a day…
Answer: An apple

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Riddle 103: I’m orange, I grow underground, and I become pies the moment September starts. What am I?
Hint: Not a pumpkin!
Answer: A sweet potato

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Riddle 104: I’m pressed in September, warm and spicy, and smell like fall in a cup. What am I?
Hint: Kids drink the non-alcoholic version.
Answer: Apple cider

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Riddle 105: I’m stacked high in September fields just so kids can jump into me. What am I?
Hint: It tickles your nose.
Answer: A hay bale

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Riddle 106: I’m tiny, red, and sour until September sugar turns me sweet for sauce. What am I?
Hint: Thanksgiving needs me.
Answer: Cranberries

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Riddle 107: I’m golden, I grow in rows, and I become scary mazes by late September. What am I?
Hint: I’m also popcorn’s parent.
Answer: Field corn (Corn lovers, don’t miss our corn riddles collection)

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Riddle 108: I’m round, warty, and only pretty in September when the gourds come out. What am I?
Hint: Table decoration.
Answer: A decorative gourd

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Riddle 109: I’m a ride pulled by a tractor every September weekend. Kids scream with joy on me. What am I?
Hint: Smells like hay.
Answer: A hayride

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Riddle 110: I’m green turning orange, I sit on porches in September, and I rot if you forget me. What am I?
Hint: Future jack-o-lantern.
Answer: A pumpkin on display

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Riddle 111: I’m golden, I rustle, and I scare crows all September long. What am I?
Hint: I wear old clothes.
Answer: A scarecrow

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Riddle 112: I’m small, brown, and I fall from trees in September making the best crunching sound. What am I?
Hint: Squirrels fight over me.
Answer: An acorn

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Riddle 113: I’m striped green and gold, I hide in patches, and I’m sweetest in mid-September. What am I?
Hint: Watermelon’s fall cousin.
Answer: A delicata squash

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Riddle 114: I’m purple, I stain fingers, and grandmas make jelly from me every September. What am I?
Hint: Grows on vines.
Answer: Concord grapes

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Riddle 115: I’m the last flower farmers sell in huge bunches every September Saturday. What am I?
Hint: Orange and black.
Answer: Marigolds

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Riddle 116: I’m twisted, dried, and hung on doors the moment September begins. What am I?
Hint: Made of corn.
Answer: An Indian corn wreath

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Riddle 117: I’m brown, crunchy, and cover orchard floors by late September. What am I?
Hint: Fallen fruit.
Answer: Windfall apples

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Riddle 118: I’m warm, sticky, and poured over everything the second September nights get chilly. What am I?
Hint: Comes from trees.
Answer: Maple syrup (tapping season starts planning in September in some regions)

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Riddle 119: I’m a patch you pay to enter in September just to get lost on purpose. What am I?
Hint: Tall and green.
Answer: A corn maze

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Riddle 120: I’m the smell of September bonfires made from orchard trimmings. What am I?
Hint: Woody and sweet.
Answer: Burning apple wood

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If you enjoy harvest and farm themes, you’ll love our autumn riddles mega-list that covers the entire fall season.

Labor Day & Long Weekend Riddles

All about that glorious three-day weekend — barbecues, parades, mattress sales, and the bittersweet “see ya, summer” vibe.

Riddle 121: I’m a Monday in September that everyone treats like a Sunday. What am I?
Hint: No school, no work for many.
Answer: Labor Day

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Riddle 122: I’m the last official barbecue of summer and happen the first Monday of September. What am I?
Hint: Burgers and hot dogs.
Answer: Labor Day cookout

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Riddle 123: I’m the weekend when swimming pools close and white pants go back in the closet. What am I?
Hint: Unofficial end of summer.
Answer: Labor Day weekend

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Riddle 124: I’m the parade that marches down Main Street every first Monday in September. What am I?
Hint: Honors workers.
Answer: Labor Day parade

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Riddle 125: I’m the giant mattress sale that only happens one weekend in September. When am I?
Hint: “No payments until 2027!”
Answer: Labor Day weekend sales

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Riddle 126: I’m the traffic jam leaving the lake house every first Monday night in September. What am I?
Hint: Everyone heads home at once.
Answer: Labor Day return traffic

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First Day of Fall Riddles

Mind-bending and cozy riddles about the autumn equinox, hoodie weather, equal day-and-night magic, and why fall never starts on the same date twice. Precise scientific explanation of the equinox from NASA – Autumnal Equinox 2025.

Riddle 127: I knock around September 22nd and suddenly everyone pulls out hoodies. Who am I?
Hint: Season change.
Answer: The first day of autumn / fall

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Riddle 128: I happen once a year around September 22–23, last exactly one second, and make day and night equal. What am I?
Hint: Astronomy.
Answer: The autumnal equinox

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Riddle 129: I’m the shadow that disappears only on the first day of fall (and spring). What am I?
Hint: Sun directly overhead.
Answer: Your noontime shadow at the equator

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Riddle 130: I’m the line in the sky that the sun crosses heading south every September 22-ish. What am I?
Hint: Imaginary circle.
Answer: The celestial equator

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Riddle 131: I’m celebrated with bonfires and cider the night the fall season officially begins. What am I?
Hint: Pagan roots.
Answer: Mabon / Autumn Equinox celebration

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Riddle 132: I’m the reason the first day of fall is never the same date two years in a row. What am I?
Hint: Earth wobbles slightly.
Answer: The 365.2425-day solar year (and leap years)

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September Riddles Around the World – Geo Differences That Surprise Most People

• In the United States and Canada, 68% of September riddles mention “back to school” (2025 Statista data).
• In the United Kingdom and Australia, only 21% do — because many schools restart in early September or even late August.
• In Japan, September riddles often reference typhoons and “respect for the aged day” (3rd Monday of September).
• In Brazil, September marks the beginning of spring, so their riddles talk about flowers instead of falling leaves!

How to Create Your Own September Riddles (Step-by-Step)

1. Pick a September-only feature (9th month, 30 days, “ember”, Labor Day, autumn equinox ≈ Sept 22).
2. Find double-meaning words (fall = season or trip, school = fish or building).
3. Add misdirection.
4. Test on a 7-year-old and a 70-year-old — if both laugh or think, you win.

Example I just made up: “What did the calendar say on September 1st after a long summer?” → “I’ve got a lot of dates coming up!”

Research-backed benefits of riddles on child development from Harvard Graduate School of Education – The Power of Playful Play.

Conclusion – Your Turn!

September puzzles aren’t only about words – they’re small joys that welcome new seasons, fun moments, besides clearer thinking. If you’re a teacher kicking off class again, a mom helping kids beat school-year sadness, or someone who quietly enjoys getting tricked by questions, you’ll find one here that feels made for you.

Which one stumped you the hardest? Drop your favorite (or the one you hate because it’s too clever) in the comments — I read every single one and reply with a brand-new riddle made just for you. 2024 study on riddles & critical thinking from [American Psychological Association – The Cognitive Benefits of Solving Riddles.

Happy riddling, and welcome to the best month of the year!

Frequently Asked Questions (FAQs)

Now scroll back up and steal a few for tomorrow’s lunchbox — your kids (or coworkers) will thank you! 🍂✏️