Tips for A Successful Family Road Trip

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Notes from Tanglewood Hideaway: Brown County Highlights – This is a weekly email I send sharing things to do, local updates, and ideas for everyday life in Brown County. 👉 [Join the newsletter here]

Sunset over rolling hills in Brown County with silhouetted trees and glowing clouds. Text reads Notes from Tanglewood Hideaway Brown County Highlights.

Do this, not that—family road trip edition. Some tips to keep your next family trip fun for everyone.

Spring Break is right around the corner, and if you’re anything like me, you’re probably deep in trip planning mode. (Or at least thinking about how you should be…)

Between hosting hundreds of families at the Barn Burner and growing up going on two-week-long family camping road trips every summer, I’ve learned a thing or two about what makes (or breaks) a family trip.

And since we’re also gearing up for a big Pacific Northwest road trip this summer, I’m back in my road trip planning groove!

So today, I’m sharing three of my top do’s (and don’ts) for setting yourself up for a smooth, fun trip—whether you’re road-tripping to Brown County or beyond. (This email may contain affiliate links.)

1. Do plan for at least one fun thing a day—but don’t overcomplicate it.

When I was a kid, my mom had one rule for road trips: no matter how far we had to drive, we’d do at least one fun thing each day. I still follow that rule now, and it makes such a difference.

This doesn’t have to mean elaborate, pre-planned activities. Just keep your eyes open and go with the flow. A quick search on Google Maps can help you find a local park or playground for a lunch stop. A quirky roadside attraction might be worth a detour. Sometimes, the best moments are the unexpected ones.

Keeping a small cooler and a picnic blanket in the car makes it easy to stop anywhere without worrying about where you’ll eat.

2. Do always pack a swimsuit, no matter where you’re traveling—don’t assume you won’t need it!

One of our family’s golden rules: ALWAYS pack a swimsuit.

Even if swimming isn’t in your plans, it’s one of those things that takes up no space but is so annoying to buy last-minute. Over the years, we’ve unexpectedly ended up at hot springs, hotel pools we didn’t realize had one, and even splash pads at city parks we stopped at for a break.

Even here in Brown County—where you wouldn’t necessarily expect a water park—there’s an indoor water park at the Abe Martin Lodge inside Brown County State Park. (If you’re staying at the Barn Burner, day passes are available!)

If it’s warm out, I extend this rule to packing water-friendly shoes. Natives are my go-to for kids because they double as everyday shoes. I live in these Archies flip flops all summer, while Clint swears by Chacos.

3. Do be okay with extra screen time—but don’t rely on it.

Road trips and screens go hand in hand these days, and that’s okay. But if your drive is more than a couple of hours, it helps to mix things up.

Our favorite non-screen entertainment:

Would You Rather?—The best road trip game. Even little kids can play, and their answers (and explanations) are hilarious. You wouldn’t believe the divisions in our family about the right answer to “Would you rather have a monkey or a dolphin as a pet?”

This book has been a favorite of ours for years, or you can download my free ‘Questions & Discussion Topics’ printable for more ideas to keep the conversations going with older kids and family on vacation.
Riddles—Once your kids are a bit older, these are perfect for making the whole car work together to solve them. I got my kids this book for Christmas and lately we’ve been working through a few every night at dinner.
Podcasts—Our favorites are Wow in the World and Ologies(or Smologies for episodes edited for younger kids). Both are great for curious kids and adults alike.
Travel games—Small, easy-to-pack games that work just as well in the car as they do while waiting for dinner.

Mixing in non-screen activities keeps the trip feeling fun and gives everyone a chance to connect.

Check out my new ‘Shop My Favorites’ page!

Over the years, I’ve tested a lot of travel gear—both for our own family trips and while hosting guests at the Barn Burner. And now, I’ve rounded up all my tried-and-true favorites in one place.

From kids travel and road trip must-haves (like the adjustable headrest supports that are saviors on long drives) to my year-round hiking essentials, our favorite outdoor gear, and more—this is the stuff I swear by for making travel easier and more fun. Take a look and see if anything makes planning your next trip a little simpler.

Happy trip planning! And if you have a favorite road trip tip or item you swear by, I’d love to hear it—just hit reply and share.

Remember, you don’t have to go far to get away.

Kara

P.S. If Brown County is on your travel list this spring, March availability is still open at the Barn Burner—including individual unit rentals if you’re not traveling with a big group. And if you’re looking for a different kind of stay, I put together a guide to some of the best cabins in Brown County (including ones with hot tubs!).

Fallen trees and twisted driftwood washed up on a beach in Jekyll Island, GA, while the sun sets and the Atlantic Ocean stretches away in the background.

Driftwood Beach on Jekyll Island in Georgia—a cool discovery on our quest to “do something fun every day” on a road trip back from Florida a few years ago. One of the most surreal and interesting beaches I’ve ever been to.