Roadschooling Day 1: It’s Really Happening…

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Jake Cain is an entrepreneur and writer from Cincinnati, Ohio. He spends his free time driving around the country in his late 90’s conversion van, affectionately known as the “Monster Van” with his wife and 3 boys.

For years, when in conversations with friends, you’d sometimes turn to fun-to-think-about topics like “You know what I’d like to do one day?” 

Then you fill in the blank with something you’d really like to do… but in reality, you’ll probably never do…

One of those things for me that’s always sounded fun was to “Pull the kids out of school one year and just travel around and homeschool them. You know… see historical stuff and make it part of the learning.”

I’d always imagine doing cool things like “This Paul Revere guy sounds like a real go-getter, how about we get out of here and go see the Old North Church he rode past?” 

I don’t know if the reality will be as cool as my imagination thinks it is, but it sounds awesome.

There are people who actually do this and make a lifestyle out of it, commonly called “road schooling.” 

Admittedly, it’s always been one thing on my list that I never thought I’d really do. After all, our kids have one of the most idyllic elementary school situations one could imagine. 

It’s easily walkable from our house, and kids can go home for lunch any day they want – which means I usually take my boys for a weekly trip to Skyline Chili on Fridays. 

(Our kids have no idea how good they have it.) 

So in a “normal” year, homeschooling our kids is something we’d never really consider given how sweet of a setup we’ve got right now. 

However, I bet I don’t have to tell you that 2020 is no normal year. 

I don’t know how the end of year remote learning went for your elementary-aged kids, but if I could sum up our experience in one photo it would be this: 

Hudson Homework
C’mon buddy… just FINISH it!

So as we got closer to the school year and my good friend, Mike DeWine, and local schools were trying to figure out exactly what school was going to look like this Fall, we had that same feeling of dread and anxiety that all of you did.

“Dear God, please tell us they have some building Hudson can go to for 30 hours per week…”

As we rolled into August, it felt like nobody really knew if kids were going to be in person all the time, some of the time, none of the time… 

One thing I do know is that I’m ever the optimist and I’m always wrong with Corona-predictions. 

“There’s no way they’ll cancel March Madness…”

“Baseball without fans? Yeah, right…”

“You don’t think kids will be back in school by Fall? You’re crazy…”

So, I’ll just say that like you, I have no idea what’s going to happen in schools this year. They might be in person all year, they could be remote next week and never go back in the building. 

You’re asking the wrong guy. 

I do know the uncertainly of it all is very stressful. Kind of like last year when my kids came running out to get in the van after school and excitedly said “Dad! they just said we don’t have school for the next three weeks!” 


But at some point along the way leading up to the 2020 school year, we did talk to a homeschooling friend who listened to our anxiety-filled predictions about the beginning of school and plainly said…

“You guys should just homeschool.”

I’m no stranger to homeschooling, I actually was homeschooled one magical 6th grade year back in the early nineties by my mom. We taught each other a lot that year. I taught her how fractions worked, and she taught me how to pick beans at my grandpa’s farm.

But despite my own homeschooling success story, this idea hadn’t really crossed our minds until a few weeks ago.  

Maybe it’s because we’ve had all 3 of our kids home all day since March, making this the longest summer of all-time.

What kind of idiot would say “this has been great, let’s do what we can to keep the kids home with us even longer…”? 

But, the more questions I asked, and the more Googling I did, the more I thought “I think we could really do this.”

Plus, I still had my beautiful 1998 Chevy Express sitting in the driveway – maybe this was destined the be the year to do that “road schooling” I always dreamed about but never really planned on doing… 

Let The Roadschooling Begin

A couple of weeks ago we made it official and pulled the kids out of school this year. 

We picked out a curriculum mix and I started planning our trip. 

We’ve been a little hush-hush about it, mainly because one of the biggest things I’ve learned during Covid is that there’s a lot of people who seem to relish the fact that tattling and being overtly rude to perfect strangers is now socially acceptable behavior.

How can I mention “perfect strangers” without a picture of these guys: 

Perfect Strangers

I’ll avoid going off on a tangent here… but let me just say if you want to confront someone who had their mask off and sneezed on you, that’s one thing. 

But if you’re the person calling 911 on a small business owner when restaurants were only allowed 10 people inside and you did a headcount and found 11… you need to reevaluate some things in your life. 

The situation of what people, from which states are allowed to visit other states and for how long, with and without quarantining or providing a urine sample changes on a daily basis. 

I’m pretty sure I stopped to go pee today in rural New York and it was perfectly legal, but if I’d have been from Florida that would have been a 3rd-degree felony…

So I debated whether or not to even share these experiences with you, in the off chance that one of you is going to call some FBI tip line and have me locked up for driving around to historical sites.

I think that it’s highly unlikely that this trip ends with me in prison for sightseeing… but it’s 2020 and I’m done making predictions. 

That said, almost every friend that I told about our plans asked me the same question…

“Are you going to blog about it?”

Yes I Am

I’ve thought about it, weighed the pros and cons, and I’m doing it. It’s hard to find the time every day, but it’s actually a lot of fun for me to write down these memories while they are fresh and reflect back on them later. 

The last time you were reading my travel blogging, we were on a month-long road trip with my parents in the Monster Van. 

I was surprised by how many of you followed along and later told me how much they enjoyed it. 

If I like writing and you like reading it, that’s a win-win-win in my book. 

from Michael Scott GIFs via Gfycat

Road School Day 1

In case you’re curious, we’re not actually going to be on the road and traveling the full year. 

The plan is still developing, but we just took off on a 5-6 week journey to the Northeastern US.

We’re hoping to see a bunch of important US history sites along the way, and having the kids read and write about them as we go. We’ll be staying in various cities for a week at a time, renting a house so we can do school in the morning and do some experiences in the afternoon. 

Like we do every year, we took some first day of school photos before we hopped in the van:  First day of school

We knew it was going to be a great first day when about 10 minutes into the trip, Sarah said “Hudson clean up your garbage”  and he replied, “I’m on lunch break.” 

After lunch break was over, Sarah sat in the back and helped the kids during reading time. Then, it was my turn to teach, and today was their Music History elective, so we did a sing-a-long to this classic:

Music History Class

(If you’re a teacher reading this, I promise that Spotify isn’t actually part of the curriculum.) 

An Unexpected Gem

I don’t venture up to northern Ohio often, and I can’t say that I’ve ever been to Mentor, Ohio before today. 

Frankly, I had no intention of going there today either. 

We were just hungry for lunch and they had 2 of those blue signs before the exit packed with a variety of restaurant logos. 

So I pulled off the exit, then I noticed a sign for a James Garfield Historical Site that was only a couple of miles away. 

I told Sarah we might as well see what it was, just hoping that it wasn’t something as dumb as Four Corners

It turns out, it was the anti-Four Corners.

It was really cool. 

Judge me if you must, but before today if you’d have asked me “Who was James Garfield” I would have probably said “one of the presidents.” 

I’m not even sure I knew that he was an Ohio guy. 

But sure enough, the Garfield family house at the time he was elected sits right there in Mentor. Here we are out front reenacting a photo on the sign below with included Ulysses S. Grant and James Garfield with two other less notable characters: 

James Garfield House

I won’t bore you with James Garfield facts that we learned today, but he seems like my kind of dude. Unfortunately, he was assassinated by some disgruntled idiot early on in his presidency. 

After watching the 18-minute video, I’m convinced he would have been a good one. 

He became famous for running a “front porch campaign” where he would just sit out on this very front porch and just shoot the bull and answer questions for anybody who wanted to stop by. It caught on, and he basically turned his front porch and his house into campaign headquarters. 

In fact, he was sitting at his desk in the little library annex they built, when he got the telegraph that he’d just been elected president in 1880. 

James Garfield Desk

It took a few minutes to get warmed up, but the kids really loved this place. The visitor center was open and we basically had the place to ourselves. It felt like there was one National Parks Ranger per visitor, ready to answer questions. 

The boys got a Jr. Ranger book and completed the activities and earned their badge. 

We even had them writing out the facts they learned about Garfield today while we were waiting for dinner, and it was rather shocking how much they remembered. 

“Did you know James Garfield lived for 80 days after he got shot?!”

The James Garfield Historical site was definitely an unexpected day 1 win.

We were just planning on doing some reading time in the Monster Van, but we snuck in some Ohio history and the kids didn’t even know what hit ’em. 

Here are some more photos from the experience: 

IMG 6216 IMG 6206 IMG 6201 IMG 6200 IMG 6193 e1599018041439 IMG 6194 IMG 6217 IMG 6230 e1599018068396 IMG 6229 e1599018110750 IMG 6228 e1599018130175

Buffalo Bills Stadium 

Another free course our kids get this year with homeschooling is Sports History 101. 

Before they were officially homeschooling, this course was simply called “riding in the car with dad.” 

Today, we took our first field trip to see what the Buffalo Bills football stadium looked like. 

Bills Stadium

Given that the Bills can’t find a sponsor for their stadium naming rights and are just calling it “Bills Stadium” and it’s in a suburb called Orchard Park, NY – you might assume that the setting isn’t anything too spectacular. 

You’d be right. 

Nevertheless, the kids are football crazy right now and any chance they get to see a big football stadium they are all about it. 

Plus, Grayson has a buddy in our neighborhood named Abe who has to be the only kid in Ohio who would say the Buffalo Bills are his favorite team. We at least had to take a picture to send it to Abe, if for no other reason. 

What’s Next

Tomorrow we’re planning to see Niagra Falls and get up close and personal with a Maid of the Mist boat ride. 

They have zero expectations other than we’re going to see some waterfall, so I’m thinking it’s going to blow their mind. 

After that, we’re journeying onward even further north and further east… 

I’ll try to keep sharing the journey as we go. 


25 thoughts on “Roadschooling Day 1: It’s Really Happening…”

  1. You guys seem to always have the time of your lives. What a wonderful education for the kids, one I’m sure they will treasure forever. I enjoy reading all abouy your experiences.

  2. I love reading your travel blogs. Your boys will never forget this. You and Sarah are awesome parents. Post lots of pictures of light houses. My dream is to travel the East coast an visit all the light houses. Be safe have a great time!

  3. Think you need a “visiting teacher”…..I could fly in and help w a few lessons! You need to collect Natl Park stamps along the way, bet you did that when west traveling.

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