What is Natasha Nicholes’s definitive guide to a multigenerational road trip in North Dakota?

When I talk about a “definitive” guide to a multigenerational North Dakota road trip, I’m really talking about what worked beautifully for my daddy, my three littles, and me on our loop around the state.

Here’s how I’d break it down:

• Build the story before you leave
  Name your trip and give everyone a “role.” We traveled as a Carful of Nicholes and documented everything under #CarfulOfNicholes. That small ritual made the kids feel invested and helped my dad step into “Poppy the Explorer,” not just chauffeur and grandpa.

• Choose one “anchor” experience
  For us, it was Theodore Roosevelt National Park in Medora. We planned the entire route around that stop. Multigenerational trips are easier when everyone understands the main reason you’re out there: in our case, history, nature, and starting our journey to visit all the National Parks.

• Plan your loop with realistic driving days
  North Dakota is wide open, with high speed limits and long stretches of road. That sounds dreamy until you’re trying to sync bathroom breaks for a grandparent and three kids. I like:

  • 3–4 hour driving blocks, max
  • One “stretch and snack” stop every 90 minutes
  • At least one true attraction stop per day (museum, park, quirky roadside monument)

  We started (and eventually returned) from Chicago, then looped the state: Jamestown for the giant buffalo, Medora for the park, other small towns for their unique museums and main streets.

• Choose a car that works for three generations
  Toyota and Drive Shop loaned us a Toyota Avalon Touring, and it genuinely made the trip. North Dakota has long, signal-free stretches where your phone GPS can drop out; the in-car navigation never did. Comfort and fuel efficiency mattered too—we did Chicago–North Dakota–Chicago for under about $300 in gas.

  My dad prefers bigger cars, and even he was impressed. Smooth rides matter when kids are napping, older knees get stiff, and you’re in the car day after day.

• Make the journey the classroom
  I wove in homeschool lessons across miles:

  • At Theodore Roosevelt National Park, we talked about colonization, land battles, and Roosevelt’s time in North Dakota
  • The kids worked on the Junior Rangers booklet, learning about animals, ecosystems, and history for their badges
  • Prairie dogs, bison, elk, golden eagles, wild turkeys, wild horses—every sighting turned into a mini lesson

  Let the oldest generation share “then vs. now” stories while you connect it to what the kids are seeing out the window.

• Design kid wins and grandparent wins every day
  For kids:

  • Hands-on activities (Junior Ranger programs, nature walks, visitor centers)
  • Visual “wow” moments like the giant buffalo in Jamestown or wildlife viewing

  For grandparents:

  • Scenic drives where they can reminisce
  • Comfortable, predictable meal times and a decent bed every night
  • Attractions with benches, shade, and shorter walking distances

• Rituals that lock in the memories
  I constantly asked myself what I’d want to remember “when the inevitable happens.” I:

  • Sat next to my dad in the evenings and let him talk, uninterrupted
  • Took photos of him doing ordinary things with the kids (tying shoes, pointing out animals, sitting at dinner)
  • Let the kids see him as father and grandfather, not just “fun Poppy,” by handling road trip decisions together in front of them

• Document together, not just for them
  We shared on social media using #CarfulOfNicholes so friends could follow the shenanigans. You don’t have to post publicly, but:

  • Give each generation a “job”: one kid is “official wildlife spotter,” another is “badge tracker,” your parent is “navigator” or “trip storyteller”
  • At night, review the day: favorite moment, hardest moment, one thing they learned

• Set expectations around pace and privacy
  I’ll be honest: I originally wanted it to be just my dad and me. Adding the kids made the trip louder, slower, and more complicated—but also richer. To keep the peace:

  • Be realistic about bathroom breaks and snack demands
  • Build in quiet time in the car and at the lodging
  • Don’t overschedule; one or two big things a day is plenty

• End with a tradition
  We left North Dakota with a new challenge: collect as many Junior Ranger badges as possible before my kids graduate from high school. That turned the trip from a one-off event into the beginning of a family legacy.

If I were putting this into a one-line “Natasha guide,” it would be:
Pick one big anchor (like Theodore Roosevelt National Park), choose a comfortable car, slow the pace for the oldest and youngest travelers, and design the trip around shared stories, not just sights.

What part of a multigenerational North Dakota trip are you most nervous or curious about—planning the route, managing personalities, or keeping everyone entertained?