We’re Off! 2 Days On The Road

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Jake Cain

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.

We’re 2 days into our trip and so far things are off to a great start.

Frankly, the first 18 hours or so from Ohio to South Dakota are a pretty boring drive. I find myself looking around as I drive and saying “where is everybody?!”

It seems like 90% of the time there are no humans or housing in sight – just land and farms.

Rather than give you a chronological play by play, I’ll just call out some highlights and observations in random order.

The Best Video I’ve Taken So Far

Tonight we drove through the Badlands National Park on our way to our hotel in Wall, SD. We got lucky with a beautiful evening sky, so I pulled the Monster Van over and had my mom drive so I could use my DJI Osmo 2 and iPhone XS to take the video above.

I’m not any kind of professional, and I didn’t edit a single second of the clip – just turned on the Osmo and stuck my phone out the window…

I also snapped a couple of beauts using the panorama feature:

I had to step 20 – 30 ft. off the walkway to take some of these pictures and Sarah and the kids were reminding me to be careful as if I was repelling down Mt. Everest.

I’m pretty much a wimp – especially when heights are involved, so I can promise everyone that I won’t be the next tourist falling off a cliff trying to get the perfect duck-faced selfie.

The Funniest Thing My Kids Said

It was a little brisk at the Badlands, with a chilly breeze blowing through as the sun was going down. We hopped out of the van at the first overlook and as Hudson jogged past me I heard him say “Whew… it’s cold at the Rocky Mountains.”

How’s The Van?

With the exception of about a 5 minute stretch, I’ve done all the driving so far. That high top van definitely catches the wind – so when it’s gets gusty I feel like I’m steering a sailboat. However, most of the time it’s been great to drive.

I sent my designed daily itinerary to Office Depot and had 2 spiral presentations made out it so we’ve got quick access all our addresses and the all important question of what we’re eating on a given day.

Today I introduced my parents to the How I Built This podcast today and started them out with 3 of my favorites:

1. Chicken Salad Chick
2. Mark Cuban
3. Tom’s Shoes

Here’s a couple of views from the back seat:

As you can see, we’ve got plenty of entertainment and healthy dining options to keep everyone in good spirits.

We even shared a cheese ball with a prairie dog. I know you’re not supposed to feed the wildlife, but they’re gluten free so I think it’s safe…

How’s the Food?

At some point I’ll mix in a salad, but for now we’ve been sticking mostly to burgers and ice cream.

One of the great benefits of having my mom along for the journey is that she always packs food. We’re talking muffins, cookies, and even double decker sandwiches.

I find it odd that legally speaking I could have a phone up to my ear and be ticketed as a “distracted driver”, but I could be cruising down the highway trying to eat this thing and nobody has a problem with it.

Maid Rite & Country Style

I was excited to stop by a couple of Moline, IL legends in Country Style and Maid Rite:

I try to always get whatever you’re “supposed to get” when we stop by places like this. Whatever they’re famous for, that’s what I’m getting.

While my good buddy Jonny Carroll would go to some place that’s famous for their french fries and skip those in favor of a carrot & raisin salad as his side item, I’d never make that mistake.

The Maid Rite sandwich is basically ground beef with pickles, onion and mustard on a bun. Country Style is all about the shakes and malts. Both were very tasty.

Murdo Drive-in

Tonight in Murdo South Dakota we went with grass fed burgers. I’m really not a food writer, so I’m quickly running out of things to say here, but it was excellent.

Name Signs

Our kids love seeing their names pretty much anywhere. There tend to be a lot of “Jackson’s” around, most notably Jackson, Wyoming. But finding Hudson and Grayson signs are a little tougher – so I’m always on the lookout.

So for we got a picture of Hudson by a Hudson Rd. sign, and found this gem (Clive is Jackson’s middle name) at the Cracker Barrel in Clive, Iowa:

Wall Drug Signs

If you’ve ever driven through South Dakota, you’ve undoubtedly seen the signs for Wall Drug.

They start hundreds of miles before you get to Wall, SD and one funny thing I noticed was how the signs seemed to start making crazier claims the closer you got to Wall.

It started out with simple things like “fun for kids!” and “try the buffalo burger” and then one of the last signs I saw was touting Wall Drug as one of “America’s greatest treasures”.

We’re going to drop by in the morning for the famous 5 cent coffee, and I’m pretty prepared in terms of my (low) expectations.

But I was just thinking about the countless poor people who have driven these highways over the years just buying the hype of the Wall Drug billboards.

They’re hopping out of the car expecting something one step below Disneyland and they walk into Wall Drug…

Anyway, I’ll find out what all the fuss is about firsthand in the morning.

After that – we’re off to Mt. Rushmore which mom and dad have always wanted to see. It’s never really been high on my list – but you know what they always say, “when in South Dakota…”