This summer, my family and I are going on a lengthy road trip vacation through the South, touching the states of Illinois, Indiana, Kentucky, Tennessee, Georgia, and Florida, and possibly portions of Alabama and Missouri. We’re intending to visit several sites along the way, including historical areas, museums, national parks, and amusement parks.
A big part of our family road trip vacations is that we plan a few “tentpole” events – big stops that form some of the destinations of our driving – but most of what makes such vacations so enjoyable isn’t those big tentpole stops, but the little things along the way.
Many days, we start off by stopping at a grocery store and refilling our cooler with some food items for the day – sandwiches, vegetables, and odds and ends like that. Then, we’re off to our destination that evening.
What makes our trips stand out, though, isn’t the race for the destination, but the fact that we’re constantly looking for little quirky stops along the way. The highlights of many of our family vacations have centered around stops at roadside attractions and serendipitous discoveries. In fact, much of our vacation planning is done to include this type of serendipitous discovery.
Why? Two reasons. One, it’s incredibly fun to find a weird roadside attraction or something really unusual in a small town somewhere. Two, it’s almost always free and, if not, it’s always super cheap, far less than the cost of going to big “attractions” in larger cities.
Want a specific example? We don’t build memories at the Mall of America. We build memories at the world’s largest twine ball in Arthur, Minn., and it’s way cheaper.
How do we incorporate this so strongly in our vacation planning?
First of all, we drive shorter legs each day than would be needed if our goal was solely to arrive at the day’s destination. For example, we could drive 12 or 13 hours in a day to make it to a destination, but we’re much more likely to just cut that in half and drive two six-hour legs, each of which provides plenty of time for stops and side journeys.
So, let’s say we’re driving from Iowa to Miami. We could drive that easily in two days if we were really pushing it, stopping somewhere in Georgia for the night. Instead, our approach would be to drive it in three days or maybe even four days, stopping along the way.
We make up for this by spending less time at the actual destination, which is often underwhelming. Plus, lodging at the destination is often expensive, whereas destinations along our road trip can often be found at a much lower price. It’s far cheaper to stay at a hotel in a nondescript area a decent distance away from a metro than it is to stay near a major tourist destination.
Our vacation planning is usually done on each day of the trip, where we scope out tools for finding unusual roadside attractions and offbeat things. We always check out and for things along our path, as well as the tourism guide for the state we’re in. We look for things that are within a reasonable radius around our driving path for the day.
For example, let’s say we’re driving from Greenwood, Ind., to Dalton, Ga., as a leg of our trip, which is about six and a half hours. As we start out for the day, we’ll check various route options on our trip and then look for various roadside attractions along the route options.
So, one route would take us close to Nashville, Tenn., while the other route would take us to the other side of Tennessee, near Knoxville. I’ll then go to and and plug in ZIP codes for some of the towns along our route, looking for interesting things near those ZIP codes.
Along one route, we might see things like the Sunsphere in Knoxville and the Big Goofy Metal Bird in Rockford, Tenn. Along another route, we might drive along Music Row in Nashville and then see the Cast Iron Cookware Man in South Pittsburg, Tenn.
The thing is, as I start naming off options along the route to our family (and, often, they’re looking at options, too), it creates a strong sense of days filled with endless possibilities. It can feel like we have tons of options, and the truth is that we’ll often stop at too many things on a road trip day like this and end up getting to our destination quite late at night because the day of road tripping was so fun and fulfilling.
Yes, sometimes the roadside attractions and weird items end up being kind of lame, but, honestly, those things often end up being just as fun. They have become the source of running jokes in our family, sometimes carried over from vacation to vacation. We still make reference to a particularly weird hotel we stayed in more than a decade ago.
On the flip side of that, sometimes you’ll find something absolutely amazing that you never expected to find. A road trip several years ago took us into Bardstown, Ky., which I’d never heard of before. It has one of the most beautiful town squares I’ve ever seen and an absolutely amazing area to walk around near the town square, and it turned out to be one of the highlights of that entire vacation even though it cost us almost nothing (we did eat a meal there, but we were planning on eating a meal in a restaurant anyway).
To bring things back around to the beginning, we often fill up our cooler at the start of the day with items from a grocery store if needed (because we often have items from the day before). This often leads us to have a picnic at a nice town square in a town we’ve never heard of before, or stopping by a playground that’s well regarded due to the unusual equipment or the giant sculpture that’s nearby. It becomes a free lunch that’s also highly entertaining and unusual.
Over the years, this has just become the norm for how we handle long road trip vacations. We used to be much more focused on the destination, but these days I find the journey to be at least as compelling, if not more so, and the journey is often far less expensive to boot. We’ve discovered all kinds of cool small town treasures over the years by doing this and it’s drastically cut into the cost of our trips, too.
If you’re planning a family vacation by car this summer, here are some suggestions to take advantage of this.
First, don’t be afraid to turn one day of driving into two or two into three, and then trim a day or two off of your time at your destination. Often, the destination is overpriced and you’ve seen everything you want to see there in just a few days anyway, so rather than spending five or six or seven days in one place, trim it down to three or four days and add a day to the drive. This allows you to cut each driving leg down substantially.
Second, fill up your cooler with stuff for a meal or two at the start of each day. Sure, you’ll probably eat at some restaurants on vacation, but if you can turn a few meals into simple picnics, you’ll save quite a bit of money. Plus, picnics tend to sync up incredibly well with interesting town squares, parks, and roadside attractions.
Third, as you start your day, take a look at and to see what you can find near you and near your route. There’s really no need to plan this in advance – it’s far more fun to let spontaneity happen and see what you’ll stumble upon on the drive. Use those tools, along with the state’s tourism guide, and identify some interesting and unusual and weird stuff along your path, and then let people talk about it and decide on what path to follow and what things to visit.
I recommend trying to include a park or a town square as one of those options for a mid-day picnic lunch. Exceptional parks and town squares often show up in tourism guides and occasionally in the other tools, too.
Finally, just enjoy the attractions, good or bad. The good ones are genuinely enjoyable. The goofy and weird and bad ones can be memorable, too, but in a very different way. Just go into these things with an open mind and you’ll usually find some things to appreciate and, if nothing else, you’ll leave with something to laugh about. More often than not, though, you’ll leave having discovered something new and interesting, and isn’t that part of the fun of a family vacation?
Never overlook the value of the roadside attraction. In fact, it’s worth your time to incorporate it into your travel plans.