Are you an adult reader looking for the top trending and most engaging stories from the beloved Sideways Stories from Wayside School series? In 2025, this collection remains a hot favorite for fans who want whimsical, hilarious, and sometimes thought-provoking tales
. From unexpected twists to quirky classroom adventures, these stories deliver everything you loved in the original series plus fresh insights perfect for grown-up readers. Each story below includes a mini Sideways Stories from Wayside School summary, making it easier for newcomers to jump in while longtime fans enjoy the nostalgia.
Dive into the top stories everyone’s talking about this year and experience the charm of Wayside School like never before.
Story 1: The Talking Chalkboard
Mrs. Jewls always had something strange up her sleeve, but the day the chalkboard started talking took the cake. It all began when Todd, the ever-curious student in the 30th-floor classroom, accidentally dropped his notebook. The chalkboard, instead of silently accepting Todd’s misstep, shouted, “Pick it up, please!” The class froze, staring at the black surface as letters rearranged themselves into sentences.
Every student had a story to tell. The chalkboard started giving advice, correcting math problems, and occasionally cracking sarcastic jokes. Joy, who normally hated class, found herself laughing so hard she nearly fell out of her chair. Even Maurecia, always obsessed with the rules, couldn’t resist the allure of a talking school tool that actually followed the rules better than she did.
The chaos reached a peak when the chalkboard offered to take attendance itself. Students lined up, waiting for the chalkboard to announce their names. By the end of the day, everyone agreed it was the best lesson they’d ever had. Mrs. Jewls, secretly delighted, knew she’d witnessed another unique Wayside moment.
Moral: Sometimes, the most unexpected voices teach the best lessons.
Story 2: The Elevator That Only Went Sideways
Louis had always been skeptical of the old Wayside elevator. Unlike normal elevators, this one only moved sideways. One Monday morning, he decided to test it. To his surprise, the elevator glided perfectly into the neighboring classroom instead of up or down.
Inside, he found his classmates participating in bizarre lessons—Bebe was painting upside down, and Rondi was juggling pencils with her toes. Louis realized that sideways movement made everything slightly off-kilter but somehow more fun. When the principal asked why everyone looked so energized, they all credited the sideways elevator.
By the end of the day, the sideways elevator became a secret hotspot for creativity, problem-solving, and pure chaotic fun. Even adults visiting for the parent-teacher meeting couldn’t stop smiling at the antics that spilled out.
Moral: A sideways approach can open doors to unexpected creativity.
Story 3: The Case of the Missing Lunches
At Wayside School, lunchtime was sacred. But one day, every student’s lunch disappeared. Detective Sammy, the unofficial investigator, took on the case. Clues led him from the janitor’s closet to the principal’s office.
After a thrilling investigation, Sammy discovered the culprit: a mischievous raccoon somehow sneaking in from the 30th floor and distributing the lunches across the schoolyard. The students turned it into a treasure hunt, racing around to reclaim their sandwiches, apples, and chocolate milk. Even Mrs. Jewls admitted it was the most engaging lunchtime she’d ever witnessed.
By the end of the day, everyone agreed that sometimes mischief could bring more joy than order. The raccoon became the unofficial mascot of the school, always a reminder that chaos sometimes has its perks.
Moral: Sometimes, a little mischief can create the best memories.
Story 4: Mrs. Gorf’s Reverse Day
One morning, Mrs. Gorf announced it was “Reverse Day.” Everything in the 30th-floor classroom had to happen backward. Students walked backward, lessons were taught from the last page to the first, and even spelling tests were given in reverse order.
Louis and Dana were initially frustrated, tripping over their own feet and scratching their heads over backward sentences. But soon, the class discovered a strange clarity in the chaos. Reading backward made them notice letters and words they’d never paid attention to. Writing backward forced creativity. Even the normally stern Mrs. Jewls got caught in the fun, laughing as she tried to solve problems backward.
By the day’s end, everyone agreed that thinking differently—even literally backward—could open new ways to learn and enjoy school. The students left with a renewed sense of imagination, eagerly awaiting the next unexpected twist in their sideways school.
Moral: A change in perspective can make learning and life more fun.
Story 5: The Mystery of the Floating Desk
One rainy afternoon, Dana noticed her desk was floating a few inches off the ground. She called Todd and Sammy over, and soon the entire class was amazed as their desks defied gravity. Papers hovered, pencils danced midair, and chairs performed slow twirls.
Mrs. Jewls, amused but concerned, investigated and discovered a tiny air vent malfunction that created a continuous upward draft. Rather than stopping the phenomenon, she allowed students to experiment with it. They wrote while balancing in midair, played floating basketball with erasers, and even raced each other from desk to desk.
By the end of the day, the floating desks became a symbol of discovery, imagination, and the unexpected joys of classroom life. Even the janitor, who had initially scolded them for the mess, admitted it was an unforgettable sight.
Moral: Embrace the unexpected—it can lift your spirits in surprising ways.
Story 6: Bebe’s Talking Shoes
Bebe was known for her style, but nobody expected her new sneakers to start talking. “Try me on!” they demanded one morning, startling her. To everyone’s shock, the shoes offered advice, comments on classmates’ behavior, and even fashion tips.
At first, Bebe was embarrassed, but the shoes became a hit. They encouraged kindness, reminded students to study, and even cracked occasional jokes that had the class rolling on the floor. Mrs. Jewls, secretly thrilled, noted it was the best morale booster she’d seen.
By week’s end, every student wished their belongings could talk. Bebe’s sneakers taught them that help can come from the most unexpected places, even from a pair of stylish shoes.
Moral: Guidance and wisdom can come from the most unexpected sources.
Story 7: The Invisible Homework
One morning, students discovered that their homework had gone invisible. Papers were blank, pencils produced nothing, and even the teacher’s corrections vanished into thin air. Panic set in, but Mrs. Jewls calmly explained that this was a chance to practice memory and imagination.
Students had to recall what they wrote and redraw their work from memory. Surprisingly, creativity soared. Sammy remembered exact formulas, Dana added new story twists, and Bebe’s invisible drawings were more detailed than ever. By the end of the day, the students realized that sometimes losing something visible could uncover hidden talents and strengthen problem-solving skills.
Moral: Sometimes what seems lost can reveal hidden strengths.
Story 8: Rondi and the Talking Locker
Rondi’s locker started speaking in riddles. Every time she opened it, it whispered a puzzle or a joke. Initially annoyed, Rondi soon realized that solving the riddles made her cleverer, faster, and even more confident in class.
Word spread, and students lined up for a chance to test their brains with the talking lockers. Even Mrs. Jewls joined in, smiling as she solved a particularly tricky puzzle involving multiplication tables and wordplay. The lockers became the classroom’s most popular attraction, blending learning with humor and curiosity.
Moral: A playful challenge can spark growth and confidence.
Story 9: Todd’s Time-Traveling Pencil
Todd discovered a pencil that could rewind and fast-forward small moments in his life. He used it to redo mistakes, replay funny events, and even pause time during a boring lecture.
The class joined in, carefully experimenting with this new tool. Laughter erupted as minor mishaps were undone, and lessons became more engaging. Mrs. Jewls observed with delight, noting that even small time-traveling experiments taught responsibility, teamwork, and patience.
By the end of the week, the pencil was safely returned to its mysterious origin, but the students had learned how to handle second chances wisely.
Moral: Opportunities to try again teach responsibility and creativity.
Story 10: The Great Sideways School Talent Show
Wayside School held its first-ever talent show—but sideways. Students performed while walking sideways, balancing on one foot, or telling jokes backward. The audience of teachers, parents, and students was amazed at the creativity and hilarity on display.
Louis juggled textbooks, Bebe danced with her talking shoes, and Dana performed a magic trick with the invisible homework. Mrs. Jewls crowned everyone a winner, proving that the joy was in participation and imagination rather than perfection.
The talent show became an annual tradition, reminding everyone that learning and fun can go hand in hand—even sideways.
Moral: Creativity and joy matter more than perfection.
Conclusion
The Sideways Stories from Wayside School continue to captivate readers of all ages in 2025. From floating desks and talking chalkboards to sideways elevators and invisible homework, these stories highlight the humor, imagination, and whimsical adventures that make Wayside School unforgettable.
For adults seeking a hot, trending collection, these tales provide nostalgia, laughter, and clever lessons. With summaries, moral lessons, and unexpected twists, these stories remain the best way to enjoy the quirks of Wayside School while discovering new layers of fun and learning.
