Earl the Squirrel’s Halloween Chess Challenge

It was Halloween night in Chesslandia and Clip and Clop were getting ready to go trick-or-treating with the pawns! They put the finishing touches on their dinosaur costumes and galloped outside.

“I hope we get treats!” Clip neighed. “Especially my favorite: candy corn!”

“What if we get tricked?” Clop asked. “We’ve never done this before!”

“Relax!” said Clip. “The pawns will show us how it’s done.”

Just then, all of King Shaky and King Chomper’s pawns raced out of their castles, decked out in fanciful costumes.

“It’s blastoff time!” Chad the Pawn said through his astronaut helmet.

When they arrived in town, jack-o’-lanterns adorned every doorstep and happy kids ran from house to house collecting candy. The knights followed the pawns to their first house of the evening and DJ the Pawn, who was dressed as a rock star, rang the doorbell.

“Trick or treat!” DJ shouted and the door creaked open…

“BOO!!!” Pat the Postwoman burst out in a ghost costume with a mailbag full of chocolates. The pawns all giggled and grabbed some candy.

But Clip and Clop weren’t so delighted. “AGHHHH!!!” they screamed. “A SCARY-BARY OOKY-SPOOKY GHOOOOST!!! RUN AWAYYY!!!”

“Don’t be scared!” Pat cried. “It’s just me!”

But Clip and Clop didn’t hear her; they were frightened to bits and galloping like the wind. They ran clear past the edge of town and into a moonlit forest.

“Phew,” Clop panted. “That was a close one!”

“No kidding,” Clip agreed. “I just hope the pawns are okay. Wait…Where are we!?”

The knights looked around and realized they’d made a big mistake. They were lost in a dark forest! On Halloween! Just before panic set in, Clop noticed a light through the trees.

“Maybe it’s a way out,” he said. “Let’s investigate.”

A moment later, the knights found themselves in a clearing lit by a flickering lantern. On the ground was a life-sized chessboard. Suddenly, a shadow began to creep toward them. The knights started to get worried again but relaxed when they saw who it was: Earl the Squirrel wearing a Robin Hood costume!

“Happy Halloween!” said Earl.

“Hi, Earl,” Clop replied, “can you help us get back to town? We got scared and lost our trick-or-treating buddies.”

“Of course!” Earl said. “But not until you’ve completed my Halloween Chess Challenge!”

Earl scampered up a nearby tree. Suddenly, gigantic candy corns tumbled down onto the life-sized chessboard below, each one landing on its own square.

“Your task is simple!” Earl continued. “Start in the corner and capture as many candies as you can. Take only what you capture! When you run out of captures, the challenge is over and I’ll point you back to town. One-two-three GO!”

Clip and Clop went gallop, gallop, step to the side, gobbling as much candy corn as they could and stuffing the rest into their saddlebags. Before long, both knights found themselves on squares where they couldn’t make another capture.

“Great capturing!” Earl exclaimed. “The town square is just past those trees. Have fun with the pawns!”

The knights thanked Earl and galloped away. When they met up with the pawns a few minutes later, they told them what happened.

“You two are so silly!” Ava the Pawn said through a mouthful of licorice.

“Oh yeah?” Clip said, grinning slyly. “Do you think…humongous candy corn is silly too?!”

Clip and Clop dumped all the extra candy corn out of their saddlebags to share with pawns. Everyone had a happy, safe Halloween. Earl’s Halloween Chess Challenge was so much fun that when they got home, they all recreated it on their chessboards!

How to Play Earl the Squirrel’s Halloween Chess Challenge:


  • Chessboard
  • One knight of either color
  • At least 63 pieces of candy corn or other small treat that fits on a chessboard square


  • Start with a clean chessboard; since you’ll be eating off of it, you may want to wipe it down with a gentle cleanser.
  • Place the knight on a corner square, as shown in the diagram.
  • Place candies on every other square of the chessboard, one per square.
  • Explain: In our special Halloween story, Earl challenged the knights to capture as many candies as they could. They got to eat (or take home) only the candies they were able to capture. Now it’s your turn to try!
  • Instruct your child to move the knight gallop, gallop, step to the side, and make a capture. (You can take turns moving the knight or let your child make all the moves.)
  • In this mini-game, captures are the only moves you’re allowed to make; landing on an empty square is not allowed.
  • Your child can eat the candies as they capture them or save them until the end.
  • Tell your child to keep capturing until they land on a square from which they can’t make another capture. When they run out of captures, the game is over.
  • After the game, shake hands and say, “Good game!”
  • Replay as many times as you like. You can also swap out candy for a healthier snack (or objects like buttons or pennies) and play this mini-game as a warmup throughout the year, not just on Halloween!
Knights Journey

For an extra challenge:

  • Keep a running tally to track how many captures your child makes before they get “stuck” on a square with no more available captures. Then play again and see if your child can increase their score by planning and thinking ahead to avoid getting stuck for longer. Note: It’s not possible to capture every single candy without getting stuck, but with the proper strategy you can certainly get close!
  • You can also hew closer to the story and play with two knights on the same board. Start the additional knight in the opposite corner and compete to see who can capture the most candies. For this variation, use knights of the same color to make it clear that you’re not trying to capture each other, only the candies on the board.

Experience the magic today!