How to Make a Headless Horseman Pumpkin

It’s one of our favorite fall traditions.

My kids would never forgive me if we skipped it!

This year I wanted to carve a special pumpkin, one celebrating my love for my favorite Halloween story of all time… The Legend of Sleepy Hollow.  

The silhouette of the Headless Horseman on his horse in the dark night stuck with me, so I decided to recreate that silhouette on my pumpkin.  

To create my Sleepy Hollow pumpkin, I followed a great tip that I learned.

Instead of carving a circle along the top of the pumpkin to open it up and scoop the flesh out, I carved a hole in the BOTTOM of the pumpkin.

 

No one will see the cuts in the pumpkin this way!

Next, I used the scooping tool to scoop out all of the pumpkin flesh and seeds.

 

This helped make the pumpkin wall thinner, which is just what I wanted.

 

I saved the pumpkin seeds to make some of these delicious pumpkin seed recipes with the kids.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Once the inside of my pumpkin was cleaned out, I painted the entire pumpkin, including the stem.

 

I wanted my Headless Horseman pumpkin and silhouette to be black, so I painted the pumpkin black with some chalkboard paint I already had.

 

I painted on two black coats of chalkboard paint, which gave my pumpkin that nice black matte finish.  

 

 

Draw the Headless Horseman Silhouette Onto the Pumpkin

To draw out my Headless Horseman silhouette, I used this silhouette as a guide.  

I drew up my design, then taped it to the pumpkin.

I traced the lines hard with a pen, so the lines would go through, then cut out the area around my design.

When I was almost done, I had a feeling that I should take a picture, even though my pumpkin wasn’t finished.  

I ignored it, then finally gave in.

I snapped a quick cell phone picture instead of one with my camera.  

As I was cleaning out the pumpkin, I dropped it.  

My Headless Horseman broke into pieces, and could not be saved. 

I was crushed (just like my pumpkin), but relieved that at least I had one picture of all my hard work.  

Please ignore the imperfections, as I wasn’t finished with my pumpkin when the picture was taken!

The Kids’ Pumpkins

My kindergartner wanted to make her VERY own pumpkin this year.

I let her carve one of the pumpkins that we grew in our backyard.  

It is small and cute, and just perfect for her!  

We cut a hole in the bottom, and scooped out the seeds and pulp.  

She drew her design onto a piece of paper first, then used a special crayon that came with our pumpkin carving kit to draw her face onto the pumpkin.

We both worked together to cut out her original design, and within 15 minutes she had her very own jack-o-lantern!  

Isn’t it cute?

She was so proud!

My little guy wanted to get in on the fun, too!

Good luck with your Headless Horseman pumpkin, and happy carving!!