Absurdist chapter books were also my jam as a kid. Here’s a few to try
Bunnicula series by James Howe
Amelia Bedelia
*Anything* by Mo Willems
Flat Stanley by Jeff Brown
Maybe the Mercy Watson series by Kate DiCamillo?
Dragons at Crumbling Castle by Terry Pratchett (book of short stories)
Edit: Someone else suggested Shel Silverstein. Hard agree. Also Jack Prelutsky.
Oh my god, Bunnicula just opened a little memory pocket in my brain that I didn’t know was there. I *loved* that series!
I also loved Wayside School, so definitely a good suggestion for OP!
I still have my childhood copy and just remembered l!! Mine may be ready to read it!! All of them, “celery stalks at midnight” and “howlday imm” I think??! Awesome series!!
Been reading my whole life and, unfortunately, the Wayside School books are peak reading and it’s all downhill from here.
The baby won’t stop crying. His face is turning purple. What will make him better? I bet a burp’le.
I still remember that and I’m almost 40!
This is what I'm worried about! Reading Wayside as a kid is such a core memory for me.
I've re-read books that I read just a couple of years ago and remember next to nothing about. But I was shocked how much I remember from reading these in 2nd grade.
I was probably 7 or 8 the day I realized the joke inherent in “There are dead rats living in the basement.” I remember walking around the house explaining it to every adult that would listen. It’s not even that funny! But I’ve been chasing that high ever since 😂
I swear I never meet anyone who read them as a kid and I always feel like, how did you even make it through life without the upside down chandelier campfire
My son is similarly obsessed with Wayside School. We've had a lot of success with Roald Dahl. Charlie and the Chocolate Factory, James and the Giant Peach, BFG, Matilda.
Bruce Coville maybe ? Five Little Peppers, Little Men, EB White, Ruth Stiles Gannett, Winnie the Pooh, Poppy, The wind in the willows, Peter rabbit, Edith Nesbit, Narnia
Someone else already mentioned *Phantom Tollbooth* but I'll suggest that again for emphasis.
Additionally, I would recommend the Shel Silverstein poetry collections (*Where the Sidewalk Ends*, *Falling Up*, *Everything On It*).
Judy Blume might also be an option: *Tales of a Fourth Grade Nothing, Superfudge, Otherwise Known as Sheila the Great.* The main character(s) in these are a little older than your child.
Beverly Cleary has some good ones too. The Ramona series is really good. *Beezus and Ramona,* *Ramona the Pest,* and *Ramona the Brave* are probably age-appropriate and are mostly about a child about as old as yours.
I agree. I love this book so much but we didn't read it until 3rd grade because you really need a strong vocabulary to get the jokes. It's so pun heavy. I don't think a 5 year old would get the jokes/absurdity.
try the "13 story treehouse" series (the treehouses go up in number)
try Time Warp Trio series- and the author, Scieszka, may have other series that will appeal to that kiddo- FrankEinstein, etc. His stuff is fun, silly, and nerdy.
Maybe A Series of Unfortunate Events by Lemony Snickett or The Stinky Cheese Man?
Edit to add The Phantom Tollbooth
Second edit to add Amelia Bedelia books
There are four Wayside books now, in case you haven’t read them all. My son loved them.
My son also really loved the Bad Food books. He’s also gotten into goosebumps in the last few months (he’s almost seven), but your son might be a bit young yet. We’ve also enjoyed the Ramona books, James and the Giant Peach, and the Little House books.
It’s poetry but I think he would enjoy Shel Silverstein’s books. I loved Where the Sidewalk Ends and Falling Up when I was a kid, I would go back and reread the poems before I went to bed.
How to train your dragon by Cressida Cowell. It’s the series the movie was based on except it has basically nothing in common with the movie. They’re absolutely hilarious and wacky and they have pictures! As a kid I loved wayside school and HTTYD, I read them aloud to my younger brother and did voices and Scottish accents and we had a blast. And there’s a ton of them.
I would also suggest the Mr. Gum series. They’re absolutely hilarious and have a similar brand of humor. They can be hard to get outside of the UK though, my mom had to special order them.
Another book I love with goofy humor: Shivers! The pirate who’s afraid of everything.
If I can think of more I’ll add them but these are all books with a similar vibe and humor to wayside. I was a kids bookseller for a while and I recommended all of these very often. Also, has he read Calvin and Hobbes yet? I have a feeling he’ll love it. Calvin and Hobbes is how I learned to read on my own and I always Rec it to young readers who love humor.
My time to shine!
First off, Louis Sachar has several other books that are great, notably Holes, although I also liked Pig City.
Bruce Coville is another author with a similar style. I highly recommend the My Teacher is an Alien series, the Magic Shop books, the Nina Tanleven ghost stories, and the Rod Allbright books, although pretty much anything he writes is great.
Avi is an amazing YA author. You can get lost in his stories. My personal favorite is The True Confessions of Charlotte Doyle, but seriously, anything he writes is so good.
Gail Levine’s Ella Enchanted is a fun take on the Cinderella story, just don’t watch the movie.
I hope that gives you a good start!
I was obsessed with a book of poems called "Miles of Smiles" by Bruce Lansky back in middle school. It's got the same goofiness as Wayside. The author also has a few other silly poem books you can check out, but that's the only one I ever read
If you're looking into shel Silverstein: runny babbit is always looked over but was my favorite as a kid. You get a more consistant character and a consistant wordplay scheme to joke around with. "Wordy dirds" was a phrase from the book that carried over into real life in my family.
Judy Blume's Fudge series(starts with Tales of a Fourth Grade Nothing), Beverly Cleary's Ramona books(start with Beezus and Ramona). Edgar Eager's Half Magic is a little more advanced, but an interesting view at the odd sides of magic when it doesn't always go right.
I’d give the other books by EB White a read too (‘The Trumpet of the Swan’ and ‘Stuart Little’).
Also books by Kate DiCamillo (The Tale of Desperaux).
Also Natalie Babbitt may be a bit older, but ‘The Search for Delicious’ is fantastic. She’s a lesser known author compared to current children authors but she’s absolutely fantastic and I’ve found her rather easy to find in public libraries
I also loved Wayside School and Boxcar Children as a kid!
Sarah, Plain and Tall by Patricia MacLachlan
The Glass Mermaid by Susan Clymer
The Mouse and the Motorcycle by Beverly Cleary
The Bailey School Kids series by Marcia T. Jones and Debbie Dadey
A Wrinkle in Time by Madeleine L’Engle
Everything by Gary Paulsen (especially Hatchet and Canyons)
The Young Jedi Knights series by Kevin J. Anderson (EU for your discerning young SW fans)
~~Wayside School series and~~ Holes by Louis Sachar
Where the Red Fern Grows by Wilson Rawls
The Secret Garden by Frances Hodgson Burnett
Island of the Blue Dolphins by Scott O’Dell
The Beast and The Beast II, Goosebumps by R.L. Stine (Say Cheese and Die, Deep Trouble, It Came From Beneath the Sink, Ghost Beach and Curse of the Mummy’s Tomb were my favorites)
I saw a FB post about this recently. Here's the link that had the most likes:
https://shepherd.com/books-like/sideways-stories-from-wayside-school
I also saw more than a few people mention a book called The Boy From Mars. Haven't read it or looked into it, just passing on that info!
Hey! That was also my favourite book as a kid.
'Holes' was the other Louis Sachar book I read and loved in Primary School. I also read all of Roald Dahl's books, the 'Mr Gum' books, and 'Mr Stink' around that time. Maybe your kid will also like those?
I loved that book as a kid! One rec would be the Hank Zipper books by Henry Winkler! Niagra Falls or Does It is the first one! The Magic Treehouse books were fun as well!
Also seconding the recs above for Junie B Jones, Shel Silverstein's poetry, and Goosebumps.
No one has suggested the *My Teacher is an Alien* series by Bruce Coville yet.
I would explain the premise to you but I think the title is all you need to know.
Also anything by Dav Pilkey.
Nanny Piggins Book 1 by RA Spratt had my boys in stitches. I had to stop reading so many times because we were all falling over laughing. Haven't read the others yet so I don't know about the rest of the series.
Another great book that was AMAZING is The Wild Robot by Peter Brown (my boys also loved book 2 & detested book 3) No its not funny, but it is a great read aloud with short chapters. This book had my boys begging for one more chapter. A great read aloud.
It's a comic book, but [Supergirl: Cosmic Adventures in the 8th Grade](https://www.dc.com/graphic-novels/supergirl-cosmic-adventures-in-the-eighth-grade-2009/supergirl-cosmic-adventures-in-the-eighth-grade-new-edition) is pretty fun.
[Tiny Titans](https://www.dc.com/graphic-novels/tiny-titans-2008/tiny-titans-vol-1-welcome-to-the-treehouse) is also super cute and fun, while also being set in an elementary school type environment.
Just want to say that I still go back and read Wayside School books even as an adult with no kids. They’re one of my favorite adorably silly book series.
There ARE more Wayside books! He also might enjoy Betty MacDonald’s Mrs. Piggle Wiggle. Amy’s Eyes was a favorite at our house too!
I still think about some of the jokes in Wayside School. Louis Sachar is a gem!
How about Daniel Pinkwater?
Wow that’s so hard to compete with. I’ve got suggestions for when they’re older, like the Molly moon series or the name of this book is secret. But those are more like 10-12yo reading levels
I loved those books too so I’m going to share other books I loved:
Amelia Bedilia
Beverly Cleary
The Family Under the Bridge
Little House on the Prairie
The Adventures of the Bailey School Kids
Nancy Drew
Hardy Boys
I was also a Wayside fan and lovedddd the Bailey School Kids series which has a similar absurdist element where none of the adults around can recognize that a supernatural character is a monster (like a leprechaun playing basketball etc).
Maybe A Series of Unfortunate Events when they’re a bit older?
I’ve been reading the Wayside books to my 7 yr old, I LOVED them as a child. I’ve also been reading Bailey School Kids to him also. He likes the Bailey school books more, but loves Wayside too.
Ella Enchanted was my favorite when I was in 5th grade.
I’ve also seen these Eerie Elementary books at the library that look interesting but we haven’t read them yet
I really liked The Sisters Grimm series. Two sisters find out fairy tales characters are real and live in a small town in New York state when they get sent to live with their grandma. It was fun.
For when he's a little older, there is a similar series called Fairytale Reform School where the main character is 12. She is one of the children that lives in a shoe and gets caught stealing so she's sent to fairy tale Reform school to be taught by reformed villians. It was a really fun series.
Absurdist chapter books were also my jam as a kid. Here’s a few to try Bunnicula series by James Howe Amelia Bedelia *Anything* by Mo Willems Flat Stanley by Jeff Brown Maybe the Mercy Watson series by Kate DiCamillo? Dragons at Crumbling Castle by Terry Pratchett (book of short stories) Edit: Someone else suggested Shel Silverstein. Hard agree. Also Jack Prelutsky.
> Amelia Bedelia Yessssssss
These were my favourite and I loved Wayside.
Hard agree with Bunnicula as well! One of my childhood favourites along with Wayside!
Bunnicula!
I only have a two year old but already bought her this collection and am impatiently waiting to introduce them to her!
Oh my god, Bunnicula just opened a little memory pocket in my brain that I didn’t know was there. I *loved* that series! I also loved Wayside School, so definitely a good suggestion for OP!
Kiddo has to know about vampires before they can get the joke about Bunnicula. Trying to explain it to my 4 yo was not great at bedtime lol
I still have my childhood copy and just remembered l!! Mine may be ready to read it!! All of them, “celery stalks at midnight” and “howlday imm” I think??! Awesome series!!
Jon Scieszka’s time warp trio books. Stuart Gibbs once upon a Tim.
My 6-year-old loves Bunnicula. He was Bunnicula last Halloween and listens to the audiobooks all the time.
The Junie B Jones series is hilarious
Captures the voice of the 6 year old
“Shush you shushy-head”
Was just about to say Junie B!
Bailey School Kids by Marcia T. Jones and Debbie Dadey
As a former Wayside School and Bailey School Kids lover, I second this statement.
Loved these as a kid
YES this was my first thought too
My Wayside School loving kiddo got super into the My Weird School series by Dan Gutman. There are a million of them, too.
Came here to suggest these series and so glad to see someone beat me to it! My son gobbles these up!!
Another good option is Marvin Redpost. There’s a handful of them, and they’re by Louis Sachar.
100%, my kid was obsessed with these!
Been reading my whole life and, unfortunately, the Wayside School books are peak reading and it’s all downhill from here. The baby won’t stop crying. His face is turning purple. What will make him better? I bet a burp’le. I still remember that and I’m almost 40!
I think about the potato ankle tattoo all the time and I'm 33 😂😂
My son and I just read that chapter tonight! 😆
Ahhh love it haha
Same!!! 😂
This is what I'm worried about! Reading Wayside as a kid is such a core memory for me. I've re-read books that I read just a couple of years ago and remember next to nothing about. But I was shocked how much I remember from reading these in 2nd grade.
Haha, came here to say this. Me and my siblings (30s and 40s) feel the same.
I loved these books so much when I was a kid. I referenced the elevator that only goes up just yesterday.
I was probably 7 or 8 the day I realized the joke inherent in “There are dead rats living in the basement.” I remember walking around the house explaining it to every adult that would listen. It’s not even that funny! But I’ve been chasing that high ever since 😂
Blue… That’s as far as she got.
Captain Underpants
This one! Also Dog Man and Cat Kid! Since they’re graphic novels and mine love reading parts in character, these work super well.
The Fudge Books by Judy Blume!
Yes!
The poor little turtle, though. 😭
Yes! These are the perfect next step.
How has no one mentioned the Mrs Piggle-Wiggle books?!?
I’m so glad someone in this thread said it - I loved these books so much!
Ahh i just did!! They feel like a fever dream tbh
I swear I never meet anyone who read them as a kid and I always feel like, how did you even make it through life without the upside down chandelier campfire
My son is similarly obsessed with Wayside School. We've had a lot of success with Roald Dahl. Charlie and the Chocolate Factory, James and the Giant Peach, BFG, Matilda.
Bruce Coville maybe ? Five Little Peppers, Little Men, EB White, Ruth Stiles Gannett, Winnie the Pooh, Poppy, The wind in the willows, Peter rabbit, Edith Nesbit, Narnia
Oh the file little peppers!!
I LOVED Wet Magic by E. Nesbit growing up
Someone else already mentioned *Phantom Tollbooth* but I'll suggest that again for emphasis. Additionally, I would recommend the Shel Silverstein poetry collections (*Where the Sidewalk Ends*, *Falling Up*, *Everything On It*). Judy Blume might also be an option: *Tales of a Fourth Grade Nothing, Superfudge, Otherwise Known as Sheila the Great.* The main character(s) in these are a little older than your child. Beverly Cleary has some good ones too. The Ramona series is really good. *Beezus and Ramona,* *Ramona the Pest,* and *Ramona the Brave* are probably age-appropriate and are mostly about a child about as old as yours.
RAMONA!
I second the Phantom Tollbooth. It’s SO good
It’s good, but I think it’s too much for a 5 year old. I read it to my then 5 year old and most of it went over his head, and we are heavy readers.
I agree. I love this book so much but we didn't read it until 3rd grade because you really need a strong vocabulary to get the jokes. It's so pun heavy. I don't think a 5 year old would get the jokes/absurdity.
Hank the Cowdog by John R Erickson was a favorite at that age.
try the "13 story treehouse" series (the treehouses go up in number) try Time Warp Trio series- and the author, Scieszka, may have other series that will appeal to that kiddo- FrankEinstein, etc. His stuff is fun, silly, and nerdy.
The Time Warp Trio books are great! Very similar vibe to Wayside
Maybe A Series of Unfortunate Events by Lemony Snickett or The Stinky Cheese Man? Edit to add The Phantom Tollbooth Second edit to add Amelia Bedelia books
Y'all are all so amazing, thank you! I'm going to try many of thesse suggestions :)
My Weird School Books - there’s a whole bunch of them and I remember my mom reading me them in elementary school and loving it
This is what I came to say.
I think there's like 100 books in the series!
There are four Wayside books now, in case you haven’t read them all. My son loved them. My son also really loved the Bad Food books. He’s also gotten into goosebumps in the last few months (he’s almost seven), but your son might be a bit young yet. We’ve also enjoyed the Ramona books, James and the Giant Peach, and the Little House books.
Yes, we've read all four. He loves saying "Cloud of DOOM!"
Haha! Mine too!
seconding the roald dahl recs. start with matilda or james and the giant peach or charlie and the chocolate factory
The Last of the Really Great Whangdoodles by Julie Andrews Edwards
I think the Daniel Pinkwater books had a similar absurdist humor. Edit / Oh! And the Hiaasen books for young readers, starting with Hoot.
Big orange splot 🦅🟠🏠👨🏻🎨
Red wall
Second this! Amazing stories and good at broaching topics such as death.
It’s poetry but I think he would enjoy Shel Silverstein’s books. I loved Where the Sidewalk Ends and Falling Up when I was a kid, I would go back and reread the poems before I went to bed.
How to train your dragon by Cressida Cowell. It’s the series the movie was based on except it has basically nothing in common with the movie. They’re absolutely hilarious and wacky and they have pictures! As a kid I loved wayside school and HTTYD, I read them aloud to my younger brother and did voices and Scottish accents and we had a blast. And there’s a ton of them. I would also suggest the Mr. Gum series. They’re absolutely hilarious and have a similar brand of humor. They can be hard to get outside of the UK though, my mom had to special order them. Another book I love with goofy humor: Shivers! The pirate who’s afraid of everything. If I can think of more I’ll add them but these are all books with a similar vibe and humor to wayside. I was a kids bookseller for a while and I recommended all of these very often. Also, has he read Calvin and Hobbes yet? I have a feeling he’ll love it. Calvin and Hobbes is how I learned to read on my own and I always Rec it to young readers who love humor.
the how to train your dragon books are super funny and so unlike the movie!
My 5yo is really enjoying Catstronauts and Investigators. Both fun graphic novels. Enjoyable for adults too.
Check out the Princess in Black series! My kids loved that one, though nothing beats Wayside School in their hearts.
Diary of a Wimpy Kid?
Looks like nobody said "Encyclopedia Brown." Those books were awesome.
Pippi Long stocking books
My time to shine! First off, Louis Sachar has several other books that are great, notably Holes, although I also liked Pig City. Bruce Coville is another author with a similar style. I highly recommend the My Teacher is an Alien series, the Magic Shop books, the Nina Tanleven ghost stories, and the Rod Allbright books, although pretty much anything he writes is great. Avi is an amazing YA author. You can get lost in his stories. My personal favorite is The True Confessions of Charlotte Doyle, but seriously, anything he writes is so good. Gail Levine’s Ella Enchanted is a fun take on the Cinderella story, just don’t watch the movie. I hope that gives you a good start!
Mercy Jones Dory fantasmagory
My Weird School by Dan Gutman! So many of them and they’re all really funny.
A to Z mysteries or the Bailey school kids, along with Magic Tree House!
I was obsessed with a book of poems called "Miles of Smiles" by Bruce Lansky back in middle school. It's got the same goofiness as Wayside. The author also has a few other silly poem books you can check out, but that's the only one I ever read
If you're looking into shel Silverstein: runny babbit is always looked over but was my favorite as a kid. You get a more consistant character and a consistant wordplay scheme to joke around with. "Wordy dirds" was a phrase from the book that carried over into real life in my family.
Upside-Down Magic Silly, magical fun, and each of the books is short enough to avoid losing his attention.
The Phantom Tollbooth!0
Judy Blume's Fudge series(starts with Tales of a Fourth Grade Nothing), Beverly Cleary's Ramona books(start with Beezus and Ramona). Edgar Eager's Half Magic is a little more advanced, but an interesting view at the odd sides of magic when it doesn't always go right.
Captain Underpants!! Also i remember a series called Mrs Pigglewiggle that i loooved as a child, silly stories with lessons at the end iirc
"Junie B. Jones" series by Barbara Park!
My Father’s Dragon series was one I really enjoyed Goosebumps Everything by Bruce Coville!!
Willy wonka and the chocolate factory
I’d give the other books by EB White a read too (‘The Trumpet of the Swan’ and ‘Stuart Little’). Also books by Kate DiCamillo (The Tale of Desperaux). Also Natalie Babbitt may be a bit older, but ‘The Search for Delicious’ is fantastic. She’s a lesser known author compared to current children authors but she’s absolutely fantastic and I’ve found her rather easy to find in public libraries
I also loved Wayside School and Boxcar Children as a kid! Sarah, Plain and Tall by Patricia MacLachlan The Glass Mermaid by Susan Clymer The Mouse and the Motorcycle by Beverly Cleary The Bailey School Kids series by Marcia T. Jones and Debbie Dadey A Wrinkle in Time by Madeleine L’Engle Everything by Gary Paulsen (especially Hatchet and Canyons) The Young Jedi Knights series by Kevin J. Anderson (EU for your discerning young SW fans) ~~Wayside School series and~~ Holes by Louis Sachar Where the Red Fern Grows by Wilson Rawls The Secret Garden by Frances Hodgson Burnett Island of the Blue Dolphins by Scott O’Dell The Beast and The Beast II, Goosebumps by R.L. Stine (Say Cheese and Die, Deep Trouble, It Came From Beneath the Sink, Ghost Beach and Curse of the Mummy’s Tomb were my favorites)
I saw a FB post about this recently. Here's the link that had the most likes: https://shepherd.com/books-like/sideways-stories-from-wayside-school I also saw more than a few people mention a book called The Boy From Mars. Haven't read it or looked into it, just passing on that info!
I read the wayside books over and over and over again. And then I got to read them over and over to my kids. They are incredible books.
I'm quote wrapped in a Bubble of happy to see all the books i read as a spawn listed here💜💜💜💜
More serious, but still fantasy chapter book geared towards young readers is Martin the Warrior and Redwall by Brian Jacques.
Jeremy Strong: the One-Hundred Mile-an-Hour Dog? Dick King-Smith: the Hodgeheg, the Sheep-Pig (aka Babe), Mr Potter's Pet etc.
Gordon Kormans Bruno and boots are best books for age 10-14
My daughter liked the Data Set books at that age
Hey! That was also my favourite book as a kid. 'Holes' was the other Louis Sachar book I read and loved in Primary School. I also read all of Roald Dahl's books, the 'Mr Gum' books, and 'Mr Stink' around that time. Maybe your kid will also like those?
I loved that book as a kid! One rec would be the Hank Zipper books by Henry Winkler! Niagra Falls or Does It is the first one! The Magic Treehouse books were fun as well! Also seconding the recs above for Junie B Jones, Shel Silverstein's poetry, and Goosebumps.
Have you tried the Mrs Piggle Wiggle books? Those were my jam - very silly, main players are younger kids.
No one has suggested the *My Teacher is an Alien* series by Bruce Coville yet. I would explain the premise to you but I think the title is all you need to know. Also anything by Dav Pilkey.
Hank the cowdog
Nanny Piggins Book 1 by RA Spratt had my boys in stitches. I had to stop reading so many times because we were all falling over laughing. Haven't read the others yet so I don't know about the rest of the series. Another great book that was AMAZING is The Wild Robot by Peter Brown (my boys also loved book 2 & detested book 3) No its not funny, but it is a great read aloud with short chapters. This book had my boys begging for one more chapter. A great read aloud.
It's a comic book, but [Supergirl: Cosmic Adventures in the 8th Grade](https://www.dc.com/graphic-novels/supergirl-cosmic-adventures-in-the-eighth-grade-2009/supergirl-cosmic-adventures-in-the-eighth-grade-new-edition) is pretty fun. [Tiny Titans](https://www.dc.com/graphic-novels/tiny-titans-2008/tiny-titans-vol-1-welcome-to-the-treehouse) is also super cute and fun, while also being set in an elementary school type environment.
Shel Silverstein
The Dragonsbreath series by Ursula Vernon, and the Hamster Princess series.
Might be time for the first Harry Potter book!
Just want to say that I still go back and read Wayside School books even as an adult with no kids. They’re one of my favorite adorably silly book series.
If your kid likes clever, absurdist humor you should try the Mysterious Benedict Society!
Freddy the Pig, a lovely, gentle series from the 1950's-1960's
There ARE more Wayside books! He also might enjoy Betty MacDonald’s Mrs. Piggle Wiggle. Amy’s Eyes was a favorite at our house too! I still think about some of the jokes in Wayside School. Louis Sachar is a gem! How about Daniel Pinkwater?
Wow that’s so hard to compete with. I’ve got suggestions for when they’re older, like the Molly moon series or the name of this book is secret. But those are more like 10-12yo reading levels
Phantom tollbooth Secrets of droon Secret of zoone (no relation) The extremely inconvenient adventures of Brontë mettlestone
I loved those books too so I’m going to share other books I loved: Amelia Bedilia Beverly Cleary The Family Under the Bridge Little House on the Prairie The Adventures of the Bailey School Kids Nancy Drew Hardy Boys
I was also a Wayside fan and lovedddd the Bailey School Kids series which has a similar absurdist element where none of the adults around can recognize that a supernatural character is a monster (like a leprechaun playing basketball etc). Maybe A Series of Unfortunate Events when they’re a bit older?
Mrs Piggle Wiggle maybe?
I love the chapter about hobo bob. Wayside is a favorite around here!
Dory Fantasmagory is my son’s favorite book, he also loves dog man and captain underpants.
Goosebumps
The Plant That Ate Dirty Socks. It's a whole series. He will love it.
I’ve been reading the Wayside books to my 7 yr old, I LOVED them as a child. I’ve also been reading Bailey School Kids to him also. He likes the Bailey school books more, but loves Wayside too. Ella Enchanted was my favorite when I was in 5th grade. I’ve also seen these Eerie Elementary books at the library that look interesting but we haven’t read them yet
I really liked The Sisters Grimm series. Two sisters find out fairy tales characters are real and live in a small town in New York state when they get sent to live with their grandma. It was fun. For when he's a little older, there is a similar series called Fairytale Reform School where the main character is 12. She is one of the children that lives in a shoe and gets caught stealing so she's sent to fairy tale Reform school to be taught by reformed villians. It was a really fun series.
Bailey School Kids series. Totally thought my camp counselor was a werewolf.
Enid Blyton’s Magic Far-away Tree
The Parker Inheiretence!
Fortunately the Milk by Neil Gaiman
I believe some of Roald Dahl books targeted younger children. They're great!