Sidewalk chalk might just be the most underrated toy of summer—and it’s the perfect invitation to get outside, move a little, and have a whole lot of fun. Whether your grandkids live down the street or across the country, these sidewalk games can help you make memories together. From hopscotch to homemade obstacle courses, there’s something here for everyone—plus a few ideas with a virtual twist for those of us loving across the miles!
In This Post
1. Chalk Obstacle Course
In-Person: Use chalk to draw challenges like zigzags, hopscotch squares, spins, and “freeze” spots.
Virtual Twist: Grandparents can draw an obstacle course and have someone film them completing it. Invite grandkids to recreate it in their driveway or sidewalk and send a video back! What a fun combo of chalk and tech!
2. Hopscotch
In-Person: Classic 1-10 board. Add silly rules like hopping on one foot or singing the ABCs. If you need a hopscotch refresher a quick google search will have you hopping in no time.
Virtual Twist: Grandparents can draw a board and “call out” numbers via FaceTime while grandkids jump.
3. Chalk Portrait Gallery
In-Person: Take turns drawing each other in chalk and adding silly features.
Virtual Twist: Grandparents can draw a self-portrait and mail a photo; grandkids do the same and compare! I have some treasured pics of self portraits my kids drew with their cousins. I’m definitely trying this one with the grandkids!
4. Shadow Tracing
In-Person: One person strikes a pose; the other traces their shadow with chalk.
Virtual Twist: Snap a photo of a shadow silhouette, text it, and challenge grandkids to guess the pose or recreate it. My husband traced the cat once, and yes we have a picture of it. It is a treasured memory.
5. Alphabet Scavenger Hunt
In-Person: Write A to Z on the sidewalk. As you find items (acorn, ball, coin), place them by the letter. Divide it up into days, or tackle all 26 items all at once.
Virtual Twist: Grandparent and grandchild each do the hunt and share photos or show-and-tell over video.
6. Sidewalk Simon Says
In-Person: Use chalk to draw colored shapes (or labeled spots) and play “Simon Says” moving between them.
Virtual Twist: Grandparent gives Simon Says commands over video call while grandkids play along in their driveway on the shapes they have drawn.
7. Chalk Maze
In-Person: Grandparents draw a maze; grandkids walk through it with a toy or scooter.
Virtual Twist: Send a photo of your maze for grandkids to recreate and solve—or turn it into a paper drawing to mail.
8. Bean Bag Toss
In-Person: Chalk circles with different point values. Toss bean bags or rocks to score.
Virtual Twist: Compete over video using the same setup, take turns, and keep score together.
9. Giant Chalk Board Game
In-Person: Draw a giant board game path. Use a die and play a “move forward/back” game. Include silly actions for my entertainment!
Virtual Twist: This one is definitely best in person, but if your grandkids create their own game, let them know you would be happy to watch, or roll the dice virtually for them.
10. Water + Chalk Fun
In-Person: Draw with chalk, then “paint” over it with water and a brush for cool effects.
Virtual Twist: Share a “before and after” chalk drawing to inspire each other with creativity.
Whether you’re playing side by side or swapping photos from miles away, these games are a sweet reminder that connection doesn’t need to be complicated. So grab some chalk, put on your favorite sun hat, and start drawing up some fun!