111+ Challenging Calendar Riddles to Sharpen Your Mind!

Ready to put your brain to the test with some time-related challenges? These 100+ calendar riddles will do just that! They’re fun, tricky, and perfect for anyone who enjoys puzzles.

Whether you’re counting days, months, or figuring out what’s hiding behind a tricky riddle, this collection will have you hooked.

Some riddles will leave you stumped, while others will make you smile once you crack them. Get your thinking cap on and dive in there’s no telling how many of these calendar riddles you’ll be able to solve. Are you up for the challenge?

(Classic Calendar Riddles)

Step into the world of timeless riddles that revolve around calendars! These classic puzzles offer a mix of tricky and fun questions, perfect for testing your logic and creativity. Can you solve them all and unlock the mystery of the days?

 

I show you the year, month by month,
I tell you when things are done.
What am I?

Answer: Calendar

I mark the time as the days go by,
Telling you when to laugh or cry.
What am I?

Answer: Calendar

I start on Sunday and end on Saturday,
Helping you keep track every day.
What am I?

Answer: Week

I hold 12 months, each with its days,
Showing you the time in many ways.
What am I?

Answer: Year

I tell you when to celebrate,
For special days I hold the date.
What am I?

Answer: Calendar

I come once a year, full of cheer,
With many holidays to appear.
What am I?

Answer: December

I mark the seasons with no delay,
Spring, summer, fall, and winter’s way.
What am I?

Answer: Calendar

I help you count the days till Christmas,
With 24 doors to open, no fuss.
What am I?

Answer: Advent Calendar

I come after January,
With days that vary.
What am I?

Answer: February

I show the date, the month, the year,
Helping you keep your plans clear.
What am I?

Answer: Calendar

I start with “J” and bring warm weather,
I’m the month you’ll remember forever.
What am I?

Answer: June

 

If you enjoy quiet moments, our Silence Riddles will be perfect for you. Then, ignite your curiosity with some Candle Riddles, rest comfortably with some Couch Riddles, and don’t forget to heat things up with Oven Riddles at the end!

 

I’m the last month of the year,
With holidays bringing cheer.
What am I?

Answer: December

I’ve got 31 days, it’s true,
It’s the month after September, too.
What am I?

Answer: October

I come after June, and my days are hot,
Vacation time, fun, and a lot.
What am I?

Answer: July

I’m short, with only 28,
But once in four years, I’m quite a weight.
What am I?

Answer: February

I hold the shortest month of the year,
And sometimes make you smile with cheer.
What am I?

Answer: February

I mark the start of the workweek,
And follow after Sunday, so to speak.
What am I?

Answer: Monday

I’m the weekend’s final day,
And the day when people relax and pray.
What am I?

Answer: Sunday

I’m the month of romance and hearts,
With flowers and love that never departs.
What am I?

Answer: February

I’m the month of spring’s first bloom,
When flowers burst from the ground in full room.
What am I?

Answer: March

I mark your birthday, year after year,
The day that brings you cheer.
What am I?

Answer: Anniversary

I’m the start of a new month’s reign,
Where some may groan and some may gain.
What am I?

Answer: The First Day of the Month

I bring the middle of the year,
A time for vacations to appear.
What am I?

Answer: June

I tell you when the school year starts,
With schedules and planning, I play my parts.
What am I?

Answer: September

I’m the last month of the summer’s heat,
With long days and sunshine so sweet.
What am I?

Answer: August

I have 30 days, and I come in fall,
With Halloween and harvest for all.
What am I?

Answer: October

I’m the month of Thanksgiving cheer,
When family gathers year after year.
What am I?

Answer: November

I’m the month when winter’s near,
And the year’s end is drawing near.
What am I?

Answer: December

I’m the month with 31 days,
The one after May, in many ways.
What am I?

Answer: June

I show you the hours, minutes, and days,
With a grid of numbers that never stray.
What am I?

Answer: Calendar

I hold the days of work and play,
Helping you plan along the way.
What am I?

Answer: Calendar

I begin the year with a fresh start,
Helping you plan with all your heart.
What am I?

Answer: January

I mark a special day with delight,
Where gifts and cake are the highlight.
What am I?

Answer: Birthday

I’m the middle of the week,
Not too far, but not quite peak.
What am I?

Answer: Wednesday

I’m often the first holiday of the year,
With fireworks and excitement in the air.
What am I?

Answer: New Year’s Day

I’m the time of year that’s filled with cheer,
When gifts are exchanged and loved ones near.
What am I?

Answer: Christmas

I’m the first month of every year,
Bringing hopes and plans sincere.
What am I?

Answer: January

I help you track the days you spend,
Counting down until the end.
What am I?

Answer: Calendar

I tell you when a new year starts,
With fireworks and hopeful hearts.
What am I?

Answer: January 1st

(Best Calendar Riddles)

Looking for the top calendar riddles? Here’s a collection of the best puzzles that challenge your mind while making you think about dates, months, and time. Test your skills with these fun and intriguing riddles!

 

I help you count the days that go by,
With months and weeks passing as time flies high.
What am I?

Answer: Calendar

I come once every 12 months,
Bringing a fresh start and new hunts.
What am I?

Answer: January

I mark the time with precision and grace,
You check me to keep up with life’s pace.
What am I?

Answer: Calendar

I’m the one that tells you when to rest,
With weekends and holidays, I’m the best.
What am I?

Answer: Calendar

I help you know the days and weeks,
So you never forget what life seeks.
What am I?

Answer: Calendar

I’m a special day that comes every year,
Full of cake, candles, and cheers.
What am I?

Answer: Birthday

I’m a month that’s full of cheer,
With gifts and joy drawing near.
What am I?

Answer: December

I bring you the start of the workweek,
After Sunday, I’m the one you seek.
What am I?

Answer: Monday

I mark the time until the year’s end,
With holidays that make spirits ascend.
What am I?

Answer: December

I’m a day that comes in the middle,
Not too early, not too little.
What am I?

Answer: Wednesday

I come at the start of every year,
Bringing resolutions that appear.
What am I?

Answer: January

I’m the one with 28 days,
But once in four years, I stretch in ways.
What am I?

Answer: February

I’m the month when flowers bloom,
When nature’s colors fill the room.
What am I?

Answer: March

I bring sunshine and summer’s glow,
When school ends, and vacations flow.
What am I?

Answer: June

I’m the month of love, hearts, and cheer,
With flowers and chocolates near.
What am I?

Answer: February

I help you keep track of every date,
From birthdays to holidays, I’m never late.
What am I?

Answer: Calendar

I mark the end of summer’s heat,
When fall begins with colors sweet.
What am I?

Answer: September

I’m the month when things cool down,
And the leaves start turning brown.
What am I?

Answer: October

I’m a time when people give thanks,
And share meals with love in their ranks.
What am I?

Answer: November

I’m the middle of the week,
With work that may make you weak.
What am I?

Answer: Wednesday

I come before the year’s last month,
A time for reflection and a festive crunch.
What am I?

Answer: November

I’m the month when summer ends,
And school starts again, my friends.
What am I?

Answer: September

I’m the longest month of all,
With 31 days, I stand tall.
What am I?

Answer: October

I bring the warmth of summer’s glow,
A time for vacations and fun to grow.
What am I?

Answer: July

I’m the month that’s filled with light,
When fireworks light up the night.
What am I?

Answer: July

I come after February,
Sometimes with extra days, quite contrary.
What am I?

Answer: March

I’m the end of the year,
With festivities and cheer.
What am I?

Answer: December

I’m the first month of fall,
With colors and coolness for all.
What am I?

Answer: September

I tell you when the holidays are near,
With special days that bring good cheer.
What am I?

Answer: Calendar

I’m the first day of the workweek,
After Sunday, I’m the one you seek.
What am I?

Answer: Monday

I’m the time to start anew,
With resolutions and plans to pursue.
What am I?

Answer: January

I mark the start of each year,
With fireworks and hopes sincere.
What am I?

Answer: New Year’s Day

I bring days that make you smile,
A time of joy and festive style.
What am I?

Answer: Holiday

I come after June and before August,
The summer heat is a must.
What am I?

Answer: July

I’m the shortest month, but full of love,
A time for hearts and joy from above.
What am I?

Answer: February

(Calendar Riddles for Kids and Adults)

These calendar riddles are perfect for all ages! Whether you’re a curious kid or an adult with a sharp mind, these puzzles will have you pondering dates, seasons, and the passage of time. Get ready for some brain-bending fun!

 

I help you know when the day starts and ends,
With months and years that never bend.
What am I?

Answer: Calendar

I come at the start of the year,
With a fresh start and hopes so clear.
What am I?

Answer: January

I mark the days you have to work,
And weekends when you can shirk.
What am I?

Answer: Calendar

I show you the weeks and days ahead,
So you don’t forget what’s being said.
What am I?

Answer: Calendar

I come in all shapes and sizes,
With dates and holidays full of surprises.
What am I?

Answer: Calendar

I’m a special day once every year,
With cake, presents, and lots of cheer.
What am I?

Answer: Birthday

I mark when summer ends and fall begins,
With leaves turning colors and winds.
What am I?

Answer: September

I’m the month with 31 days,
With festivals and sunny rays.
What am I?

Answer: October

I’m the one with holidays galore,
And presents that you can’t ignore.
What am I?

Answer: December

I come once every 12 months,
A chance for a fresh start and new hunts.
What am I?

Answer: New Year’s Day

I’m the month when love is in the air,
With hearts and flowers everywhere.
What am I?

Answer: February

I mark the start of each new week,
When you return to work, so to speak.
What am I?

Answer: Monday

I’m the middle of the week,
When the days are neither strong nor weak.
What am I?

Answer: Wednesday

I’m the last day of the week,
When relaxation is what you seek.
What am I?

Answer: Sunday

I’m the month when school begins,
And the weather starts to cool from within.
What am I?

Answer: September

I’m the time when pumpkins appear,
And Halloween is near.
What am I?

Answer: October

I bring summer fun and sun,
A time for vacations and everyone.
What am I?

Answer: June

I’m the month of fireworks and fun,
The middle of the year has begun.
What am I?

Answer: July

I’m a day that you wait for all year,
A special one that brings great cheer.
What am I?

Answer: Birthday

I’m the time of year with turkey and pies,
When families gather and time flies.
What am I?

Answer: November

I’m a month with lots of rain,
And flowers that start to bloom again.
What am I?

Answer: April

I bring days that are long and bright,
When the sun stays out late at night.
What am I?

Answer: Summer

I come after spring and before fall,
A time of harvest for one and all.
What am I?

Answer: Autumn

I show you when to take a break,
With special days for your sake.
What am I?

Answer: Calendar

I mark the time when winter is here,
With cold and snow, and holiday cheer.
What am I?

Answer: December

I’m the month when days are short,
And cold winds are the winter’s report.
What am I?

Answer: January

I help you track the days that go by,
With weekends to relax and months to fly.
What am I?

Answer: Calendar

I start the workweek with a bang,
Helping you know when the weekend will hang.
What am I?

Answer: Monday

I’m the month with 28 days,
But in a leap year, I stretch my ways.
What am I?

Answer: February

I mark the change from day to night,
A time to rest and regain your might.
What am I?

Answer: Nighttime

I’m a day that’s filled with cheer,
Where gifts and joy will soon appear.
What am I?

Answer: Christmas

I bring holidays with lots of fun,
And family time for everyone.
What am I?

Answer: December

I’m the month that brings new hope,
When people start to climb and cope.
What am I?

Answer: January

I’m the month with spooky sights,
Where ghosts and goblins come to fright.
What am I?

Answer: October

I’m the middle of the year’s time,
With vacations that are sublime.
What am I?

Answer: June

I mark a fresh start every year,
With new goals and resolutions clear.
What am I?

Answer: New Year’s Day

(Editor’s Pick Calendar Riddles and Answers)

 

I help you plan the days ahead,
Marking holidays and when to get out of bed.
What am I?

Answer: Calendar

I’m the month of love and hearts,
With roses and chocolates in all parts.
What am I?

Answer: February

I start the year with resolutions and cheer,
A time for new beginnings and hope that’s clear.
What am I?

Answer: January

I’m the day to mark your special year,
With cake, gifts, and people near.
What am I?

Answer: Birthday

I’m the month when pumpkins appear,
And ghosts and goblins come near.
What am I?

Answer: October

I mark the middle of the week,
When you’re halfway to the weekend’s peak.
What am I?

Answer: Wednesday

I bring the heat of summer’s sun,
The time for vacation and endless fun.
What am I?

Answer: June

I’m the last month of the year,
With joy and presents bringing cheer.
What am I?

Answer: December

I’m the month when school starts again,
And summer’s fun begins to wane.
What am I?

Answer: September

I’m a time for rest, fun, and play,
A break from work to refresh each day.
What am I?

Answer: Weekend

I come after January,
With days that bring warmth and merry.
What am I?

Answer: February

I’m a special day for all to enjoy,
Filled with fun, laughter, and joy.
What am I?

Answer: Holiday

I mark when summer turns to fall,
With colors changing, and cooler calls.
What am I?

Answer: September

I’m the time when leaves turn gold,
And stories of harvest are told.
What am I?

Answer: Autumn

I’m a month with 31 days,
When spooky costumes fill the maze.
What am I?

Answer: October

I’m the middle of the workweek grind,
Not too far from the weekend, but you’ll find.
What am I?

Answer: Wednesday

I’m the month with the shortest days,
When chilly winds make their ways.
What am I?

Answer: December

I help you count the days until the end,
With weeks of joy and days to spend.
What am I?

Answer: Calendar

I’m the first day of the year,
With fireworks, joy, and lots of cheer.
What am I?

Answer: New Year’s Day

I’m the month when things heat up,
With long days and sunshine in a cup.
What am I?

Answer: June

I’m the time when family gathers near,
To share food, love, and holiday cheer.
What am I?

Answer: Thanksgiving

I mark the end of summer’s heat,
With cooler days that can’t be beat.
What am I?

Answer: September

I’m the day when you finally relax,
And leave behind the weekday tracks.
What am I?

Answer: Saturday

I come with 31 days, it’s true,
And always follow the month of June.
What am I?

Answer: July

I bring days of crisp, cool air,
And the harvest season is in full flare.
What am I?

Answer: Autumn

 

For more information on the history of the calendar and how it’s evolved over the centuries, check out this detailed article on History of the Calendar.

 

I’m the month when you gather around,
And count your blessings to be found.
What am I?

Answer: November

I’m a time of year with turkey and pie,
With family and friends who come by.
What am I?

Answer: Thanksgiving

I bring the middle of the year,
With sunshine, fun, and plenty of cheer.
What am I?

Answer: June

I’m the month when summer ends,
And school begins again with friends.
What am I?

Answer: September

I’m a month of sunny days,
Where fun and warmth fill the ways.
What am I?

Answer: June

I mark the end of the year’s fun,
With lights and gifts for everyone.
What am I?

Answer: December

I’m the month with 28 days,
But in a leap year, I stretch my ways.
What am I?

Answer: February

I’m the month when love is in the air,
With gifts and affection everywhere.
What am I?

Answer: February

I mark the time to rest and play,
With weekends and holidays along the way.
What am I?

Answer: Calendar

I start the week with a fresh new start,
And give you motivation to play your part.
What am I?

Answer: Monday

I’m the one that tells you when to work,
And when to stop and be a perk.
What am I?

Answer: Calendar

Final Thoughts!