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Back to School Sidewalk Chalk Obstacle Course

Published: Aug 11, 2026 by Morgan Β· This post may contain affiliate links Β·

Create an easy Back to School Sidewalk Chalk Obstacle Course for kids with fun movements like hopping, jumping, spinning, balancing, and more! This simple first day of school activity is a fun way to make going back to school feel a little more exciting.

The first day of school comes with a LOT of feelings. Whether your kids are excited, nervous, or a little bit of both, I love finding simple ways to make the day feel special.

This Back to School Sidewalk Chalk Obstacle Course is such a fun way to kick off the new school year!

All you need is some sidewalk chalk and a driveway or sidewalk. Draw the course the night before school and surprise the kids in the morning, or let them help you create and color it.

I colored mine while my kids were at school the first day!

I love sidewalk chalk obstacle courses because they're easy to customize and get kids moving with simple activities like hopping, jumping, spinning, balancing, and pretending.

Plus, there's something extra fun about walking outside on the first day of school and finding the whole driveway decorated just for you!

back to school sidewalk chalk obstacle course

Back to School Sidewalk Chalk Obstacle Course

You can make your obstacle course as long or short as you'd like depending on the space you have. Here are all of the obstacles I included in our back to school version!

Start: Back to School!

Every obstacle course needs an official starting point!

I wrote START - BACK TO SCHOOL at the beginning of our course to kick things off.

You could also add the school year, your kids' grades, their names, or a simple "First Day!" message here.

first day of school sidewalk chalk obstacle course

Alphabet Hop

Time to hop through the ABCs!

I wrote all of the letters of the alphabet scattered around the sidewalk. I jumbled mine up, but you could put them in alphabetical order if you'd like.

Kids can simply hop from letter to letter, or make it a little more challenging by having them find and hop on the letters in alphabetical order.

You could also call out letters for younger kids to find as they go!

first day of school sidewalk chalk obstacle course

Practice Your Scissor Skills

This might be my favorite back to school obstacle!

I drew a pair of scissors followed by a long dashed line that zig-zagged back and forth across the sidewalk.

Instead of actually cutting, kids get to pretend they're the scissors and follow the dashed line with their feet!

It's a silly play on those scissor skills worksheets kids do at school and an easy way to add a follow-the-line section to your obstacle course.

first day of school sidewalk chalk obstacle course

Hop on the Apples

You can't have a back to school theme without some apples!

Apples are surprisingly easy to draw with sidewalk chalk. I made mine almost like red hearts with flat bottoms, then added a little stem and leaf to each one.

Arrange the apples like a hopscotch course and let kids hop their way across them.

first day of school sidewalk chalk obstacle course

Jump Over the Pencils

Next up: pencils!

I drew big pencils horizontally coming in from alternating sides of the path.

Kids can jump over each pencil as they make their way through, or zig-zag around them instead. Let them decide how they want to tackle it!

first day of school sidewalk chalk obstacle course

Spin Like a Pencil Sharpener

No sidewalk chalk obstacle course is complete without a spinning obstacle. Kids LOVE a spin!

For this one, I drew a big pencil standing vertically beside a giant spiral.

Have kids stand on the spiral and spin like a pencil sharpener!

They can spin around a few times before heading to the next obstacle.

first day of school sidewalk chalk obstacle course

Ruler Balance

I love following a spinning obstacle with a balancing obstacle. Being a little dizzy makes the balance beam much more fun!

For this one, draw one long rectangle and add tick marks along the sides to turn it into a giant ruler.

Kids can carefully walk heel-to-toe down the ruler like they're walking across a balance beam.

Try not to fall off!

first day of school sidewalk chalk obstacle course

Drive the Bus

Time to head to school!

I drew the front half of a school bus and let the kids take it from there.

They can pretend to hold a steering wheel and drive the bus, honk the horn, yell for everyone to get on the bus, or come up with their own silly ideas.

This is a fun imaginative obstacle to add after all of the hopping, jumping, spinning, and balancing.

first day of school sidewalk chalk obstacle course

Have a Great First Day!

Finish the obstacle course with a big HAVE A GREAT FIRST DAY!

You could add stars, hearts, balloons, school supplies, or whatever else your kids love around the finish line.

Then they're officially ready for the first day of school!

first day of school sidewalk chalk obstacle course

This Back to School Sidewalk Chalk Obstacle Course is such a simple way to add a little fun to a morning that can otherwise feel rushed or overwhelming.

And that's what I love about sidewalk chalk activitiesβ€”you don't need elaborate supplies or a huge amount of prep to make something feel special to kids.

Draw it the night before and surprise them in the morning, make it together as a fun back-to-school activity, or leave it on the sidewalk for neighborhood kids to enjoy.

However you make yours, I hope it brings a little extra excitement to the start of a brand new school year!

Tips for Drawing a Sidewalk Chalk Obstacle Course

You definitely don't need to be an artist to make a fun sidewalk chalk obstacle course, but a few little tricks make it easier to draw, easier for kids to follow, and last a little longer!

  • Double-draw your letters. Write each letter normally with one color, then go over it again slightly offset with a second color to make it look thicker. It makes the words MUCH easier to read from a distance and makes everything look more colorful.
  • Don't bother coloring everything in. Sidewalk chalk gets used up surprisingly quickly when you're filling in giant shapes! Outline your apples, pencils, stars, and other pictures and only add a little color where you really want it.
  • Use whatever sidewalk chalk you have. Any chalk will work, but this sidewalk chalk set is by FAR my favorite. It comes with tons of colors, I love the sharp points for drawing details, and the square shape makes the pieces really easy to grip.
  • Buy chalk when you see it on sale. We go through a LOT of sidewalk chalk, so I grab extra boxes whenever I find a good deal.
  • Store your chalk in a plastic bin with a lid. I dump all of our chalk loose into a plastic storage bin. It's easy for the kids to grab whenever they want to play, and the lid helps keep moisture out so the chalk lasts longer.
  • Draw the course on dry pavement. Chalk is much brighter and easier to draw with when the sidewalk or driveway is completely dry.
  • Check the weather first! There is nothing quite like spending forever drawing an entire obstacle course only to have a summer thunderstorm wash it away 20 minutes later. Ask me how I know.
  • Let the kids help. If you don't want little helpers slowing down the actual drawing, outline everything first and then hand over the chalk for them to add colors and decorations. It keeps them involved without making the setup take forever.

Thanks for reading!

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Morgan

Hey there, I'm Morgan, the creative mind behind CelebratingWithKids.com! As a parent of two lively little ones, I've made it my mission to turn ordinary days into extraordinary adventures, sharing playful activities, thoughtful toy reviews, and delightful printables to help families celebrate every moment together. πŸŽ‰πŸ‘¨β€πŸ‘©β€πŸ‘§β€πŸ‘¦πŸŽˆ

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