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Our Epic 11-State Cross Country Road Trip: September 2021

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at eastern market in detroit, a native american child boldly raises her fist in a power salute in a bright turquoise and orange mural painted on a white brick wall cross-country road trip

It’s September, and we’re heading on our epic 11-state Cross Country Road Trip.

11-state cross country road trip
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We’re going to Boise. (Sign up for the newsletter and you’ll learn why.)

We’ll be going pretty much straight west to get there, crossing Illionois, Iowa, Nebraska, South Dakota, Wyoming, and landing in Idaho.

From there, we’ll take a hard right and head north, heading back through Montana, North Dakota, Minnesota and Wisconsin.

We’re stoked.

We invite you to tag along through every stage of the trip. You can either get our weekly newsletter, or watch the updates on our Facebook page, our Insta feed, or our Twitter feed.

Or go crazy and sign up for all of them: @headroamer is the handle.

This post will be short, as I’ll be adding as we go. Here’s what we have so far:

Our Cross Country Road Trip: The Inspiration

For years, I’ve owned Road Trip USA: Cross-Country Adventures on America’s Two-Lane Highways, by Jamie Jensen.

Check out this cool graphic from the Road Trip USA website.

Heading west, we’re hewing pretty closely to The Oregon Trail.

Coming home, it’s about 500 miles (approximately 1/6th) of The Great Northern.

Why? Read on.

Our Cross Country Road Trip: The Impetus

I need to be Boise, Idaho about mid-month.

Steve needs to be in Wisconsin towards the end of September.

Why? Subscribe and follow along with us!

Our Cross Country Road Trip: The Planning Part

So when this whole thing came up back in the spring, I said, hey, Steve. I gotta go to Boise. Why don’t you come with me?

And then I said, and why don’t we drive instead of fly?

We’ll hit 5 states I’ve never been to, plus another 5 I haven’t been to in a while. Not that I’m counting, but….

Of Course I’m Counting.

I do that.

Despite my saying I’m not a List Traveler, who am I kidding? I LOVE racking up more tiles in the “How Many States/Countries Have You Visited” game board.


I told Steve the only way the trip would work is if we savor it along the way as much as possible.

From home, Boise is 24 hours and change of driving.

We could, reasonably, get to Boise in 3 days.

We could UNreasonably get to Boise in 2.

We’re taking 6 days.

It gives us a day to check out Mt. Rushmore—I could skip it, but, like, we’re there—and Crazy Horse Memorial, which I absolutely want to see. And a full day at Teton National Park.

(Street art and Native American history: 2 things I’m most excited about on this trip. This child lives on a wall at Eastern Market in Detroit. I love them so much.)

at eastern market in detroit, a native american child boldly raises her fist in a power salute in a bright turquoise and orange mural painted on a white brick wall cross-country road trip

And a relatively chilled out pace overall.

We can check out all sorts of groovy borderline Hidden Gem destinations: Dubuque, IA, and Casper, WY look promising. We’ll get some decent walk/hikes in.

By the time we get to Boise, I’ll be doing my thing all day and Steve will get a break from me.

He’ll be hitting the bars big time, throwing peanut shells on the floor, tossing back local craft beers.

(I kid my husband, of course. Also, Steve’s travel indulgence? Local Pastry. Always. No Matter Where.)

(Also? We’ll be updating our September 2021 Global Cuisine Picks as we go. Including Pastries We Meet Along the Way.)

Here’s our planning checklist, which is pretty darn simple:

  • Put thing we have to be at for a definite date as the mid-point.
  • Pencil in big stuff, like the National Parks.
  • Add in the time we need to get to the parks in a reasonable, non-ass-killing day of driving.

Of course, I’ve had an absolute ball researching, which entailed:

  • Deciding what from the Road Trip book looked worthwhile
  • Making sure Said Worthwhile Thing still exists
  • Giving Steve time to noodle and add in a few surprises he’d come across en route
  • NOT over-scheduling: The truest Slow Travel tenet in play here is the one that gets really, really selective. We’ve got, at most, 2 things in a day to check out. But in general, there’s one kind of highlight where we’ll put on savoring energy.

Also something to know?

We started planning this in MAY.

In other words, give yourself plenty of time.

Head your grouchy self off at the pass. This needs to be super cool and fun.

September 2021 Destinations: Packing for the Great American Road Trip

There are all sorts of guides for All the Things You Should Do to Get Ready for a Road Trip.

Things like, get your car serviced. Copy your vaccination document. Make sure you have AAA.

From the Berlin Wall, a place not on our list, but a picture that nicely sums up my unrelaxed posture while driving, and completely counters Steve’s exceptionally relaxed posture. Mawwiage!

We particularly like this list from Well Planned Journey (We’re using it ourselves.)

So we’re not going to talk about those type of essentials.

The thing I really wanted, a road trip packing list that made the most of our vast experience road tripping, I had to write.

It aims to cover the things that are less driving related.

How to keep your sanity. Create home away from home.

The stuff where, far from home—and often far from things we take for granted—makes you yell, DAMMIT. Why didn’t we pack that?

Coming soon to a website near you: Our Road Trip Packing Essentials Guide. If you subscribe to the newsletter? You’ll get a free a worksheet and checklist you can use for your own trip. Plus ENDLESS, weekly joy when you’re informed of our latest posts.

Already subscribed? You’ll be getting an email with a special offer just for you. And THANK YOU.

Win win, I tell ya.

Let the Road Trip Begin!

I’m writing this at 4:30 a.m. We’re getting in the car at 7 a.m.

Steve is sleeping soundly, so I’ll doubtless get a little snooze in sometime before our first stop.

Which will be….?

Watch this space.

September 2021 Destinations: Thanks for Reading!

Do you have experiences, stories, photos, and/or videos to share? Post them to the Head Roam Facebook page, or connect with us on Twitter or Instagram! Or leave a comment.

Any requests for next month? Whether or not we’ve been there, we love your suggestions. And we’d be thrilled if you want to let us run your stories and/or visuals.

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