Keepsake Reads: Graduation Picture Books Teachers Can Sign Each Year

Ft. A list of 20+ thoughtful alternatives to Oh, The Places You'll Go

May 17, 2025

∙ Paid

Graduation season is here, and with it comes the search for the perfect keepsake book to honor your littles’ growth year after year. Oh, The Places You’ll Go has typically been the most popular pick, but there are so many other picture books that offer just as much heart, hope, and inspiration ~ many of which share more inclusive and diverse messages, too.

When I taught first grade, there were several parents who dropped off a sealed manila envelope with a book tucked away inside. Their instructions were to leave a message to their child and sign the book. They would hold on to the book and repeat this with all of their child’s teachers at the end of every school year until the child graduated from high school. Upon high school graduation, they would gift them this special book with notes from all of their teachers over the years who led them up to this moment.

While my littles aren’t of school age yet, this has become one of my favorite end-of-the-school-year traditions that I’ve seen gain in popularity (and one that I intend to facilitate for my own children as well). By the time graduation comes around, the book becomes more than just a story~ it becomes a treasured time capsule filled with personal notes, memories, and encouragement from the people who shaped their early learning years.

In this post, I’m sharing 20 thoughtful alternatives to Oh, The Places You’ll Go that make perfect keepsake books to use for this tradition. Check out these stories that reflect a wider range of experiences and identities ~ I hope you find one that your child will love revisiting for years to come!

P.S. And beyond the Paywall at the end, paid subscribers will find 7 Bonus titles and a Bonus Craft Printable to pair with *Maybe* by Kobi Yamada

A List of 20 Graduation Keepsake Picture Books

Find the Full Shoppable Book List on Amazon | Bookshop. Or click on the individual titles linked below.

Be You! by Peter H. Reynolds | An uplifting celebration of individuality that encourages children to embrace their uniqueness, stay curious, be brave, and live authentically. This one reminds young readers that there's only one you~ and that's something truly special.

One Day by Joanna Ho | A tender letter from a mother to her son filled with hopes for his future. Celebrates courage, kindness, and emotional strength, reminding young readers that they are more than enough just as they are.

The Blur by Minh Lê | Framed as a superhero origin story, this book captures the whirlwind of childhood and the bittersweet joy of watching kids grow up way too fast.

Yay! by Jessica Kulekjian | A joyful celebration of everyday moments, big and small, that deserve a “yay!” From successes to setbacks, this book encourages kids to embrace all their experiences with positivity and pride.

You Will Do Great Things by Amerie | Features the imaginative journey of a young boy exploring his dreams and heritage through family photos. This picture book celebrates courage, connection, and the endless possibilities ahead ~ and is a touching tribute to the strength we carry from those who came before us.

This is a Moment by Micah Player | This book is a vibrant celebration of life’s meaningful moments that shape who we are. The story honors bravery, joy, change, and growth, and shares the reminder that every moment matters on the journey ahead.

What the Road Said by Cleo Wade | A poetic and comforting guide for life’s journey that reminds readers that it’s okay to feel uncertain or make mistakes. This book encourages kindness, curiosity, and the courage to keep moving forward—even when the path isn’t clear.

Why Not? by Kobi Yamada | An inspiring and beautifully illustrated book that encourages readers to dream big, be brave, and believe in their potential to make a difference.

Maybe by Kobi Yamada | A beautifully illustrated celebration of each child’s unique potential and endless possibilities. It gently reminds readers that they are one of a kind and encourages them to believe in themselves and their dreams.

You’re Here for a Reason by Nancy Tillman | A heartfelt reminder that each of us plays a vital role in the world. It gently reassures readers that they are here for a special reason and that life would be incomplete without them. A beautiful celebration of self-worth and belonging.

Sometimes You Fly by Katherine Applegate | Celebrates the effort behind every meaningful achievement, from a first birthday to graduation, honors childhood milestones, and encourages perseverance through successes and setbacks.

Road Like a Dandelion by Ruth Krauss | A playful collection of witty one-liners celebrating nature and imagination. This book invites readers of all ages to find joy in simple moments, and sparks creativity and wonder.

Yay, You! by Sandra Boynton | With humor and simple wisdom ~ plus occasional hippos ~ this book encourages readers to embrace new paths without overwhelm.

Will the Pigeon Graduate? by Mo Willems | A hilarious and heartwarming graduation story where the determined Pigeon faces challenges and proves he’s ready to graduate ~ maybe! Packed with humor and inspiration, it’s a fun celebration of big achievements and new adventures.

Soon, Your Hands by Jonathan Stutzman | Follows three neighboring families and their young children discovering who they are and what they can become. Through gentle, hopeful text and glowing illustrations, it celebrates the endless potential and unique stories each child will create. A heartfelt ode to family love and growth.

What Will You Be? by Yamile Saied Méndez | Guided by her abuela’s love and encouragement, a young girl explores all she could become. A joyful tribute to family, dreams, and self-discovery.

I Believe I Can by Grace Byers | A powerful affirmation of self-love and confidence for children of all backgrounds. This book is a beautiful gift for celebrating identity, hope, and possibility.

I Am More Than by LeBron James | An empowering, rhyming picture book that encourages kids to believe in themselves, chase their dreams, and recognize their potential and worth.

You Are Ready by Eric Carle | . With Eric Carle’s signature animal illustrations, this book encourages readers to embrace change, face challenges with courage, and believe in themselves. A gentle reminder that the world is waiting—and you are ready.

Wherever You Go by Alexandra Penfold | Celebrates the big and small milestones in a child’s life ~ from everyday moments to graduations ~ through vibrant illustrations and lyrical text. Centered on love, kindness, and community, it’s a touching tribute to growing up and being proud of who you are.

What We’re Reading this Week

A mini update of what’s being read in our household (and to keep us accountable to reading for fun!)

Me: Finished So Over Sharing by Elissa Brent Weissman, started One Crazy Summer (The new graphic novel version!)

Husband: Eat What You Kill by Sam Taggart (Is this a horror novel, or a carnivore diet guide? Neither! It’s a business/sales book: How to become a sales carnivore!)

Toddler: We’re Going on a Present Hunt by Goldie Hawk (Yes, I’m aware that it’s mid-May and this is a full-on Christmas book, but it’s currently the only book Toddler will let use read)

Baby: Richard Scarry’s Colorful Cars and Trucks by Richard Scarry (This one calms her down in the car almost instantly!)

Keep reading with a 7-day free trial

Subscribe to MaiStoryBook to keep reading this post and get 7 days of free access to the full post archives.

MaiStoryBook

Keepsake Reads: Graduation Picture Books Teachers Can Sign Each Year

Ft. A list of 20+ thoughtful alternatives to Oh, The Places You'll Go

A List of 20 Graduation Keepsake Picture Books

What We’re Reading this Week

In case you missed it…

Keep reading with a 7-day free trial