Sleepy Hollow Halloween Countdown Calendars Free Printable

Get ready to celebrate Halloween in the hauntingly fun world of The Legend of Sleepy Hollow! Our Sleepy Hollow Halloween Countdown Calendars are designed to capture the eerie charm of Washington Irving’s classic tale and the thrilling spirit of the movie Sleepy Hollow.

Ichabod Crane Hallowen countdown calendar puzzle framed and displayed on a wall with a black bat.

The Legend of Sleepy Hollow has always been one of my favorite stories, and it’s also a movie I love. I wanted to create a Halloween countdown calendar that would be a fun tribute to this timeless tale.

And something to be loved and enjoyed for an older audience, I mean, I can’t be the only one who is an adult and also loves all things victorian, macabre, and literary?

What’s Included?

These countdown calendars are perfect for building excitement throughout October with a unique puzzle piece to add each day. Once all the puzzle pieces are added the picture is completed!

Sleepy Hollow Halloween countdown with the headless horseman printed and laying on a black blanket with plastic skeleton hand and skull, candles, and books.

This free printable set includes 12 different puzzle-themed countdown calendars, all inspired by the book and the movie:

(2) Ichabod Crane
Brom Bones
Katrina Van Tassel
The Church
The Town of Sleepy Hollow
The Sleepy Hollow Woods
(5) The Headless Horseman

Each countdown calendar comes with:

Katrina Van Tassel Halloween countdown puzzle and puzzle pieces.

A Puzzle Board: A base design where each puzzle piece fits.

Puzzle Pieces: Each day, starting October 1st, your child (or the Sleepy Hollow fan in your life) can add a new piece to the puzzle, slowly revealing a complete image by October 30th.

It’s a creative way to build anticipation for Halloween night, with designs ranging from spooky woods and galloping horsemen to the whimsical characters of Sleepy Hollow.

How to Use the Sleepy Hollow Countdown Calendars

Print the puzzle board and pieces on sturdy paper or cardstock.
Cut out the puzzle pieces and store them in a small envelope or box.
Every day in October, add a new puzzle piece to the board until you reveal the full image on October 30th—just in time for Halloween!

Why Choose a Sleepy Hollow Countdown?

Whether you’re a fan of the book or the movie, these Sleepy Hollow countdown calendars are perfect for adding a little spooky magic to your October celebrations.

It’s a family-friendly activity that offers daily fun as you count down the days until Halloween. Plus, the anticipation of slowly completing the image add to the excitement!

Sleepy Hollow themed Halloween countdown calendar puzzles.

Other Fun Ideas to Add to a Sleepy Hollow-Themed Halloween Advent

Want to take your Sleepy Hollow Halloween countdown to the next level? There are a few other things you can include to make it even more memorable. Let’s make this Halloween season a fun and engaging one!

The headless horseman halloween countdown puzzle displayed up on a wall.

1. Daily Sleepy Hollow Games & Activities: Add a fun fact or trivia question about The Legend of Sleepy Hollow with each puzzle piece. Or have fun with Sleepy Hollow themed games and activities together like Bingo, Go Fish, Tic Tac Toe, or Memory!

2. Sleepy Hollow-Themed Treats: Pair each day’s puzzle piece with a themed treat like “Headless Horseman” cookies or pumpkin-flavored goodies.

3. Read-Aloud Story Sessions: Read or listen to a chapter from The Legend of Sleepy Hollow or share an excerpt from Washington Irving’s works to go along with the countdown.

Katrina Van Tassel Halloween countdown calendar puzzle completed and framed.

4. Costume Dress-Up Days: For extra fun, add dress-up themes like wearing something inspired by Ichabod Crane or Katrina Van Tassel on certain days of the countdown.

5. Cinema Night: Watch the movie “Sleepy Hollow” streaming on Prime (for more mature audiences). Or watch Disney’s 1949 “Ichabod and Mr. Toad”.

By incorporating these ideas, your Sleepy Hollow Halloween countdown can be transformed into a full-on advent celebration that will thrill Sleepy Hollow fans of all ages!

How to Download the Free Printable

These Sleepy Hollow Halloween Countdown Calendars are free and available exclusively to our email subscribers.

Simply sign up, and sign in, to gain access to this countdown along with other Halloween printables.

The Legend of Sleepy HOllow Halloween countdown puzzle with watercolor scenes of characters and places in the book.

The Legend of Sleepy HOllow Halloween countdown puzzle with watercolor scenes of characters and places in the book. The churchyard scene in a spooky nighttime woods.

The Legend of Sleepy HOllow Halloween countdown puzzle with watercolor scenes of characters and places in the book. The headless horseman riding through sleepy hollow woods.

The Legend of Sleepy HOllow Halloween countdown puzzle with watercolor scenes of characters and places in the book. Ichabod Crane's Portrait, a tall man in a spooky forest.

The Legend of Sleepy HOllow Halloween countdown puzzle with watercolor scenes of characters and places in the book. Katrina Van Tassel's portrait, a woman with long blonde hair wearing a black and white striped dress.

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