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Every year my family takes an epic cross-country road trip. We started calling it “Big Trip” and the name stuck.  This year is Big Trip Lucky 13. (I’m not too superstitious but it just seemed like a good idea to hedge our bets and add “Lucky” to the name for this year.)  We’ve been driving the same minivan since the beginning and while it’s doing great, it certainly is no spring chicken.  Ol’ Faithful (for lack of a better name!) is currently 225,000 miles old.  We’ve had a few car-related hiccups over the years (ask for a re-enactment of the breakdown in Alabama sometime) but generally travel without trouble.

We started taking these roadtrips as a way to maximize family visits.  As a family of 5 we could either fly to visit one set of grandparents each year which means we see each set only once in three years. Or we could drive and see all of them every year. (This great plan was crafted over a dinner date at a local Mexican restaurant.  I wasn’t even the one drinking the margaritas but still agreed to drive my young children (ages 2 – 6) across the country mostly by myself. Hmm…)

The first trip was a success so we kept it up.  Every summer for the last 13 years in fact.  We (almost) always go to Illinois, Colorado, New Mexico and Texas each summer.  But life is short and there are SO many things to see.  If I’m going to drive 5,000 miles every summer, I want to see something different each time.  There is more than one way to get from Virginia to those places and back again.  I would even venture to say that there are more than 13 ways! Every year we drive past even more things that we haven’t seen yet so I write them down in my notebook to be added to the list for future trips.  “Next time!” I always say.

Using an atlas and my notebook to record my travels
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Keeping notes in my notebook as we go.

Back to the main question at hand… How do I find such fun places to stop?

Every year when I post pictures of our journey on Facebook, people will ask how I find such cool or unusual places to visit.  They also sometimes ask me to plan their next road trip for them.  My reply to these comments- 1. It’s complicated.  And 2. they may not really want me to plan their next trip because there is a lot of driving to be done between these cool and unusual stops.  Our trips are generally 3 weeks or more and we cover on average at least 5,000 miles.   Of course, it is definitely possible to still plan a delightful road trip on a smaller scale using these same tips.  Just because I can’t keep my trips to less than 5,000 miles doesn’t mean everyone has to go to such extremes to explore and enjoy our country.

Always on the alert

If you are considering a road trip at any point in your future, I recommend that you start a list of some sort to keep track of any potential places you might like to visit.  If I see something mentioned on Facebook or in a news story that sounds like it might be interesting to visit, I look it up online then add it to my Big Trip bookmarks folder.  At the end of each trip I also go back through my notebook to find the places I noted as potential future stops and add these to the bookmark folders.  Another option would be to save things onto a board in Pinterest.  (Here’s a nice article by The Misguided Millennial on using Pinterest for travel planning.)

using bookmarks to keep track of potential future waypoints on big trip
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A glimpse into my bookmark files for potential Big Trip waypoints. I have a folder for every state. From the Ohio folder I have already been to the field of giant corn cobs, William Howard Taft National Historic Site, the Santa Maria replica ship, and the Rock and Roll Hall of Fame (though I haven’t taken the kids there yet – I went myself on a work trip back in the pre-kids days).

Planning Resources

My annual notebook is my main resource for the detail planning for each trip.  I plot out the days and mileage here during the planning stages then keep a daily journal during the trip.

I use my road atlas for a big picture view of the states/country during planning but not as much now as in the early years.  At this point, I’ve got a pretty good idea of where we’re headed and the various main routes to follow.

  • SIDEBAR: As we drive, I use the GPS 99% of the time but keep the atlas in the car.  We’ve used it a couple times when bailing out of a traffic jam at the last second and ending up on back roads.  The Google Maps app is pretty good about re-routing you and finding the fastest route but it’s always a good idea to have a non-technology dependent backup plan.

Beyond paper and pencil, there are several websites I use when planning the next big trip.

Google Maps

This one is pretty obvious.  I use Google Maps mostly for figuring out mileage/travel time between various places.  Also to look for hotels along the way, near where I might want to stop for the night.

googlemaps will tell me the travel time and mileage for the fastest route
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Using GoogleMaps to calculate the time and mileage for the fastest route between two points on our trip. This is just the starting point. Now I can plan the specific route and points of interest along the way.

Roadside America

This is a good place to look for those random, quirky, quick stops along the way.  In my opinion, the search features are not optimal for the way I personally plan my trips but it does offer a multitude of places to see in every state.  Definitely worth checking out when looking for interesting stops along the way.  Fun things I’ve found by searching Roadside America:

  1. World’s Largest Ball of Twine
  2. World’s Largest Easel
  3. World’s Largest Mattress
  4. World’s Largest Duncan Phyfe Chair

(are you noticing a trend?  Haha!)

roadside america is a great source for off-beat points of interest for your next big trip
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Roadside America is not a fancy website. It even feels a bit clunky sometimes. But it is most definitely a great source for off-beat points of interest.


New this year!  I tried out Roadtrippers.  There are several features that I like but still don’t find it to be a 100% complete planning resource.  One thing that I did like about using Roadtrippers was that I can easily toggle various stops on/off in the list or rearrange the list to see how it affects my total route travel time and mileage.

I downloaded the app to my phone so that I could access my saved itineraries while on the road.  This worked as long as I had a cell signal or wifi (which is something I can’t count on always having). One complaint I have about the app is that once we were on the road I wasn’t able to search easily for new destinations.  I could search for things nearby my current location but I couldn’t search for points of interest along my route the way I can when using Roadtrippers on the computer.  (Update – Actually, I can search this way.  I emailed customer service to find out if it’s possible.  The answer is yes.  Obviously it isn’t completely intuitive how to do this since it took multiple exchanges with the company to find the answer to my exact question.  So that moves Roadtrippers up on the list as a good planning tool.)

using roadtrippers to plan my big trip route
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Using Roadtrippers to find points of interest, adding, subtracting, and rearranging as I go. I usally have more places to stop than is realistic. Onto the list they go for “Next time!”

Use coupon code BTR5QTP to save $5 on your Roadtrippers Plus membership

(affiliate link)


Not all my planning is done with a computer.  I also like to look at books for ideas.  Libraries typically have many books in the travel section.  Some years I check out a few and look through them for ideas.  As always, anything that looks interesting gets added to the bookmarks folder for future reference.  When we first started our annual Big Trips, the kids were younger so I would specifically look for books that covered things kids would like to see or do, such as the Fun with the Family series.  Another book I bought many years ago is 1001 Places to See in US and Canada Before You Die.

That’s it, in a nutshell.  Basically, it’s a case of “Constant vigilance!” as Mad-Eye Moody would say.  I’m always on the lookout for things I haven’t seen yet and keeping a list.  So much to do, so much to see!

What about you? Do you have any tips for planning an epic road trip?  Share in the comments!


Because I’m all about seeing behind-the-scenes, I thought you might enjoy a little peek into the making of my cover photo for this post.  I don’t usually put this much effort into my photos but since I needed to take a specific picture for this one purpose, I figured I’d try to get a good one.  And as the saying goes- In for a penny, in for a pound!  Are there other things I should have been doing with my time today?  Yes. Always.  But, at the very least, the living room has now been vacuumed.  That chore has been on my list for a couple weeks (yes, I’m a terrible housekeeper, it’s true) and now it’s done.  A total win if you ask me.

road trip planning tools with messy living room in the background
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Here’s how things look in my living room as I’m staging attempt #1 to get a good cover photo for my road trip planning post.
road trip planning tools on table
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Cover photo attempt #1. It looks okay but the chair ring impression in the corner is bothering me. Then after I edit the photo, I decide that the see-through table may not be the best option. I might as well just go down to the floor for less visual clutter in the photo.
road trip planning tools on table with vacuum cleaner to the side
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If I’m going to use the floor, then I’m going to need to vacuum. Ryan and Rocco are “helping” me.
road trip planning tools lying on floor
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In for a penny, in for a pound! I’ve moved my items to the floor, rearranged some furniture, and added light reflectors (the back side of a poster we used for scheduling the graduation mayhem last spring and tablecloths that were originally used for a big party last fall – recycling and making do at it’s finest!) around the sides. Now it’s Felisa’s turn to help!

And now for the final result…

travel mascot and road trip planning tools
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An assortment of tools to use when planning your next epic road trip! Don’t forget your travel mascot!


Want to plan an epic road trip with quirky and interesting stops along the way? Check my tried and true planning process used year after year for our family road trips across the US
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