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Dannelle Gay · Aug 3, 2026

The Traveling Cheesehead’s Unofficial Rules for Great Road Trips

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Dannelle Gay · Dannelle Gay

After hundreds of thousands of miles on the road, I’ve learned a few things.

  • Some of them the easy way.

  • Some of them...not so much.

So if you’re planning your own adventure, here are my completely unofficial, highly opinionated rules for a great road trip.

  • Always leave room in your suitcase.

You’ll find the perfect vintage jacket, an armful of books, local coffee, handmade pottery, or something you didn’t know you needed until you saw it in a tiny thrift store.

Search “thrift stores near me.”

Every.

Single.

Town.

  • Eat where the locals eat.

If the parking lot is full of pickup trucks at 6:30 in the morning, you’re probably about to have a fantastic breakfast.

  • Take the detour.

The road everyone else skipped is usually where the best stories are hiding.

  • Talk to people.

The museum volunteer.

The pie baker.

The bartender.

The park ranger.

The cashier at the hardware store.

Ask one question:

“What do tourists usually miss?”

Then listen.

  • Never judge a restaurant by its sign.

Some of the ugliest buildings I’ve ever walked into served meals I’ll remember forever.

  • Always order the local specialty.

Even if it sounds a little odd.

Especially if it sounds a little odd.

  • Take fewer selfies.

Take more pictures of ordinary things.

  • Menus.

  • Old signs.

  • Storefronts.

  • Your muddy shoes.

Those are the photos that bring memories rushing back years later.

Put your phone away once in a while.

GPS can get you there.

Looking out the window lets you experience it.

  • Collect stories instead of souvenirs.

Although...if you happen to find an incredible thrift store...

Buy the jacket.

Finally, remember this.

  • The destination is only part of the trip.

The road between destinations?

That’s where life usually happens.

Happy travels...

And if you happen to see me wandering through a tiny thrift store or chatting with someone over a slice of pie, stop and say hello.

I’ll probably have room for one more story…

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