167 Fun, Silly & Deep Road Trip Questions for the Family

By Joshua Davis •  Updated: 02/13/22 •  15 min read

If you’re looking for a fun way to keep your family entertained on a road trip, look no further!

Rather than just spin off a lengthy list of plain ol’ road trip questions that you could ask, we have compiled those AND fun-fueling activities that will make the time fly and create a more enjoyable time in the car for everybody.

Whether you’re heading to visit loved ones, taking your next vacation, or car camping in the great outdoors, questions like the ones below will make sure everyone has a great time.

You can even use these ideas when you are stuck inside during bad weather or if you just want to do something different with your family. The best part is that these ideas are low-cost-to-no-cost; so, your wallet can enjoy the trip too.

road trip questions

Road Trip Questions and Road Trip Conversation Starters

After you’ve put some miles behind you, it can become difficult to keep the conversation going. Before you know it, everyone (except the driver, of course) has become phone zombies, interacting with their screens more than each other.

Maybe you’ve been stuck in the car for hours with your family and the kids are bored out of their minds. Maybe you’re just trying to get everyone off the screens and engaging each other. Whatever the case, it can be a challenge to get the conversational ball rolling!

Turn to OFHQ’s favorite family tradition for the road: conversation starters! These car ride questions will help get that stubborn ball rolling and keep everyone entertained during your journey.

Random Road Trip Questions

  1. What is the most hilarious sound you can make?
  2. What is the most hilarious face you can make?
  3. Isn’t cereal really a soup? What do you think?
  4. What secret society would you like to form?
  5. What do you wish others could see that is invisible?
  6. What’s the funkiest odor you’ve ever experienced?
  7. Why aren’t hotdogs and hamburgers just called sandwiches?
  8. What is the scariest movie you’ve ever seen?
  9. What is something that everyone looks funny doing?
  10. What’s the most embarrassing thing that has ever happened to you?
  11. What is the weirdest dream you’ve ever had?
  12. Imagine animals could talk: which one would be the rudest?
  13. Which legendary creature would improve the world most if it existed?
  14. What inanimate object would you most like to delete from the world?
  15. What is the most unusual thing you’ve seen in someone else’s house?
  16. What would you consider the most terrible name for your kid?
  17. What would some of the cheat codes be in life if it were a video game?
  18. Instead of war, what ridiculous activity could countries participate in to settle differences?
  19. What would the world look like if it were populated with male and female versions of yourself?
  20. What is something that’s really popular now, yet in 5 years everyone will be embarrassed by?

Deep Road Trip Questions

  1. What one thing would you change if you could alter anything from your history?
  2. If money and time were not issues, what would you do for a living?
  3. What is your favorite childhood memory? And why is it significant to you?
  4. What do you need right now to make yourself happy for the rest of your life?
  5. What is more mind-boggling: the notion that we are alone in the cosmos, or the hypothesis that we aren’t?
  6. If your phone could get internet reception from 10 years in the future, what would you search for first?
  7. What would you say to your younger self if you had the ability to go back in time?
  8. What was a tiny act of kindness you were once shown that will stay with you forever?
  9. Is money capable of bringing us joy?
  10. What one thing would make the world a significantly better place?
  11. What do you think you will be doing in 20 years?
  12. If you had been born in the late 1800’s, what do you think you would have spent your time doing?
  13. There’s a restaurant called Karma. It doesn’t have a formal menu. You only receive what you deserve. What are they going to serve you?
  14. If Home is more of a feeling than a place, then what is Home to you?
  15. The world will end in 2 hours and you’ve been invited to board the only shuttle to colonize Mars. You can only bring three things with you. What are they?
  16. What would you do if you had $100,000 to help others?
  17. When was the last time you felt absolutely fulfilled?
  18. You come upon a time machine. What period of history do you travel to and observe firsthand?
  19. When have you experienced the most gratitude in your life?
  20. What do you consider to be the most important invention ever?
  21. When do you feel most alive?

Would-You-Rather Road Trip Questions

  1. Would you rather be the most famous person but helplessly poor or richest person and nobody know you exist?
  2. Would you rather own a national park or a theme park?
  3. Would you rather be completely paralyzed but have the most brilliant mind in the world or have a perfectly functioning body and be the least intelligent in the world?
  4. Would you prefer to eat a little can of cat food or two rotten tomatoes?
  5. Would you rather be completely bald or completely coated with hair?
  6. Would you rather have to skip all the time or run all the time?
  7. What do you think about having hooves instead of feet?
  8. Would you rather have your grandmother’s hairstyle or middle name?
  9. If you had to choose, would you rather drink all of your meals from a baby bottle or wear obvious diapers for the rest of your life?
  10. Do you want to speak in rhymes all the time or sing all the time instead?
  11. If you had to choose, would you rather hug a snake or kiss a jellyfish?
  12. Would you rather have to smell rotten flesh or skunk all of the time?
  13. What sort of face do you want? Would you choose a pig nose or a monkey face?
  14. Would you prefer to swim in shark-infested seas or free fall with a parachute into the Grand Canyon?
  15. Do you prefer to eat a peanut-butter and tuna sandwich or three live earthworms?
  16. Do you wish to own a ferocious dragon that breathes fire, or do you want to be the most terrifying fire-breathing dragon?
  17. Would you choose to be a clumsy ninja or a wizard with amnesia?
  18. Would you choose long yellow beaver teeth or no teeth at all?
  19. Would you rather have to forget your favorite memory or your best friend?
  20. Do you prefer having a nightmare every night or never be able to dream again?
  21. Would you prefer to be able to softly murmur all the time or only be able to loudly shout all the time?

Road Trip Questions Conveniently Packaged

These packaged games will have the family laughing and learning all about each other in no time.

#1 501 Questions: A Travel Game: Second Edition

501 Questions: A Travel Game: Second Edition
$14.99
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05/22/2022 12:17 am GMT

In Short:

This game is about talking as a family and having a blast doing it. Aside from just passing time on a road trip, you can make the time count with enjoyable, enlightening, and often hilarious discussions with your family.

More than 750 questions (249 were added for the 2nd edition) are organized into four categories:

  1. Would You Rather . . . ?
  2. If You Could . . . ?
  3. Tell Me About . . . ?
  4. Travel Trivia

This innovative travel companion was created by Lindsey Nubern in response to her own necessity to engage her family while on the road and has helped many families make the travel experience much more than just a boring car ride.

#2 Talking Point: Conversations with Purpose

200 Unique Question Cards in 5 Categories, Wholesome Conversation Cards for Kids & Family
$29.97
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05/22/2022 12:17 am GMT

In Short:

Looking for an interesting, unique, and engaging way to get to know your family better? Look no further than Talking Point: Conversations with Purpose.

This card game is designed to help you build trust and confidence with your loved ones while having fun conversations that are tailored for all ages. With 200 questions in 4 categories to choose from, you’ll never run out of things to talk about.

Categories include:

  1. Get to Know You
  2. Family Time
  3. What Makes You You
  4. Fun and Random

So, load up the car or gather the family around the dinner table and break out Talking Point for hours of entertaining dialogue.

#3 Let’s Mingle: Family Edition

Road Trip Essentials Conversation Starter Cards for Families
$7.95
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05/22/2022 12:21 am GMT

In Short:

Let’s Mingle: Family Edition is a card game that helps promote a growth mindset, problem-solving skills, and mindfulness. At the same time, it draws the family together in a conversation that is comfortable and enjoyable.

If coaxing more than one-word answers out of your kids is like pulling teeth, you’ll want to give Let’s Mingle” a try. With 110 questions about family and life, it’s a great way to spark interesting conversations with even the most hesitant members of your family.

Each round, one person draws a card and asks the question on it to another player. The goal is to ask follow-up questions to get more detail.

The deck of cards has a nice mix of funny and serious questions that are family-friendly and sure to liven up a drab time on the road.

#4 Let’s Mingle: Kids Edition

Let's Mingle Kids Card Game
$18.95$13.95
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05/22/2022 12:27 am GMT

In Short:

Let’s Mingle: Kids Edition is a game that helps establish mindfulness values in younger children. The game is designed to help kids learn how to interact with others, while also promoting a growth mindset and problem-solving skills.

Let’s Mingle: Kids Edition is a great way for families with younger children to spend quality time together. It can also be played by a parent and child or two kids on their own.

Conversation Starters in Game Form

You’re on a road trip with your family and you’ve been driving for hours. The kids are getting antsy and you’re all needing something more than just a conversation.

Here are some of our favorite ideas for things to do in the car while on a road trip.

#5 MadLibs on The Road: World’s Greatest Word Game

Mad Libs on the Road: World's Greatest Word Game
$4.99
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05/22/2022 12:19 am GMT

In Short:

What makes MadLibs so great is that they are a fun way to build reading comprehension and grammar skills and encourage everyone to collaborate toward a common (crazy) goal.

Each story is a chance for the family to work together to create unique stories. Write in the missing words on each page to create your own hilariously funny stories all about road trips, travel, and other activities.

For more outrageous plots, pass the book around and take turns filling in the blanks.

Once your family has completed all the stories, the finished work makes for great memories to read through on future road trips.

#6 Briarpatch Travel Scavenger Hunt for Kids

Briarpatch Travel Scavenger Hunt Card Game for Kids
$9.99
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05/22/2022 12:17 am GMT

In Short:

The Scavenger Hunt for Kids is the ideal boredom buster and ideal passenger for your next family adventure. You’ll be asking where all of the time on the road went thanks to cards that keep your eyes, ears, and even nose occupied!

Scavenger Hunt for Kids has 54 See It, Hear It, and Smell It cards, making it a multi-sensory game that can be played repeatedly with family and friends no matter where the journey takes you.

#7 Shotgun!: The Road Trip Game

Shotgun! - The Hilarious Family Card Game for Road Trips
$14.99
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05/22/2022 12:21 am GMT

In Short:

If you’re looking for some friendly competition in the car, look no further than Shotgun!

Players earn points by completing unique and innovative travel-conducive tasks on each card such as being the first to get people in a passing car to wave back. Other cards deduct points for things like being the next one to ask, “Are we there yet?”

The drawstring storage pouch makes this ideal for keeping it in your glove box so it’s always at the ready.

#8 Do You Really Know Your Family?: A Fun Trivia Game About Your Family

Do You Really Know Your Family? Conversation Starters and Challenges
$24.99
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05/22/2022 12:37 am GMT

In Short:

Do You Really Know Your Family? is a game that lets you learn more about your family and have tons of fun in the process!.

With this game, families will be able to laugh and learn new things about each other through trivia questions while sparking interesting conversations.

You might think you know everything there is when it comes down to your family; but, this card game proves otherwise!

#9 Lifetime Inc. Road Trip Kit

Road Trip Travel Games Activities
$22.99
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05/22/2022 12:25 am GMT

In Short:

VARIETY is the Road Trip Kit’s flagship feature.

Chocked full of different games and reusable activities the whole family can play or the kids can use to entertain themselves, it is a great way to keep kids busy and happy while traveling.

The kit includes probably close to $50 worth of materials and activities if they were purchased separately. If one activity gets old, there are plenty of options to keep things from getting monotonous and enjoyable.

A unique feature of this kit is that it provides a kid-friendly way for them to keep track of the trip’s progress so they know how much longer you’ll be on the road.

#10 Carpool Chaos

Carpool Chaos - Play While You Ride
$29.99
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05/22/2022 12:17 am GMT

In Short:

Carpool Chaos is a card game that takes the boredom out of car rides. Designed for families with older children (10 years +), with 160 large cards, Carpool Chaos is sure to keep you entertained for trips on end.

This game specializes in the random, wacky, and absurd when it comes to getting everyone to think outside the box, sparking conversations that are sure to generate some laughs.

friends on a road trip

What are some good road trip ideas?

If you’re looking for a fun way to spend some quality time with your family, a road trip is the perfect option. Not only does it allow you to explore new places, but it also provides the opportunity for some great bonding experiences.

To make sure your road trip is as enjoyable as possible, be sure to bring along some fun games and activities. Whether you’re looking for something to keep the kids busy or something that will get everyone laughing, we’ve got you covered.

So, grab some of the ideas we mentioned in the article above and hit the road! You’re in for a memorable adventure.

What is the most important thing you should consider before taking a road trip?

Arguably, the most important thing a person should consider before taking a road trip is if they have enough money. Make sure you have enough cash for gas, food, lodging, and any other emergencies that may come up.

That being said, a detailed budget for your trip is critical:

Spend time forming an in-depth budget for your trip so that you have a dependable estimation of what the total cost will be.

Nothing ruins a good road trip like running out of money!

Wrapping Up Road Trip Questions

Road trips are the perfect opportunity for family bonding and getting to know each other better. It would be a shame to let all that valuable time pass with everyone in their own little “screen worlds.”

The journey itself can bring families closer together, especially when you have some conversation starters on hand. Whether you’re looking for something fun and funny, thought-provoking or would-you-rather, we’ve got you covered.

And when the typical list of conversation starters won’t do the trick, liven it up with the fun road trip questions in convenient travel game form! Who knows, you may have heard, “Are we there yet?” for the last time!!

Now, get out there!

Joshua Davis

Being outdoors is freedom! Being outdoors with my wife and two boys is LIVING! Whether in my backyard or getting lost in a National Park, there’s nothing I’d rather do than explore, discover, and experience the paradise that surrounds us. Give me my family, a backpack, and a trail and my life is full!