After years of visiting major American cities on various city breaks and then spending some time travelling across America on small group escorted tours, I was really starting to tick the 50 states of America off, having even managed to visit Alaska which isn’t part of the ‘Great 48’ mainland states. A visit to Denver, Colorado marked reaching my 30th state (ok, some states I’d just passed through without stopping at at this point, but it still kinda counted!) and it seemed silly now not to try and aim to tick off all 50.
Looking at a map, it became clear that the majority of the states I had left to visit, were congregated around the middle – the Midwest states – and as it seemed to be agreed on most travel sites that there wasn’t a lot to see in this part of the USA, none of the small group tours I looked at visited any of these in much detail, if at all.
Having made a great group of friends on the tours I had previously done, I began to see if any of these would be interested in adding to the number of states we had visited and eventually, this lead to a group of 3 of us deciding to plan our own tour, a roadtrip of the Midwest states, lasting around the 3-week mark.
We were all drivers so would hire a car, plan a route and take it in turns to drive each day. The aim was to tick off the states in the middle and find our own adventures along the way, proving the websites which said there was nothing to see in these states wrong!
Having never planned a trip like this before – we were all used to jumping on a group tour and having everything done for us – we were unsure where to start but having seen our tour guides in action, how difficult could it be driving across America, getting to places on time and finding interesting places to stop at along the way, right?
Deciding that Chicago would be a good ‘gateway to the Midwest’, we began to plot a possible circular route passing through as many states we hadn’t yet visited as possible before arriving back in Chicago.
Iowa, Nebraska, Kansas, Oklahoma, Arkansas and Missouri were all on our list and, similar to our Trek trips, we decided to aim to spend just one or two nights at each stop along the way.
We had very little idea on what each of these states had to offer but we’d heard of St Louis, Missouri and all wanted to visit its Gateway Arch and one of us knew someone who had visited a Wizard of Oz-themed attraction in Kansas which sounded like fun – who doesn’t like the Wizard of Oz after all – so we added those ideas to our list as a starting point.
Wanting to try and recreate the feel of our Trek America trips, we also made a list of all the activities we had enjoyed on these tours so that we could find similar opportunities along the way this time – National Park visits, white water rafting, horse riding, bike or Segway tours… were all jotted down on a document we had created and shared via Google Drive.
On our Trek America trip across the Northern states, we had spent a lot of time travelling through South Dakota but never made it across the border into North Dakota. It was a bit out of the way, to say the least, of the other states we were aiming to cross off this trip but as we were unsure when else we would ever get there, we started to look into whether we could somehow add it into our itinerary.
Remembering a brief couple of hours stop we’d had at Wisconsin Dells on our Trek America trip, we thought we could factor in a longer stop there after leaving Chicago then from there it made sense to once again pass through the state of Minnesota from which we could travel up into North Dakota before heading south through South Dakota and into Iowa to begin our original circular route back to Chicago.
So that is where we began, with 2 nights pencilled in in Chicago then 2 nights in Wisconsin Dells. I’d heard a lot about the Mall of America with its indoor amusement park which sounded like fun so we pencilled in a 2 night stop in Minneapolis.
Thinking of Minnesota reminded us of the random stop we had made during our Trek America trip at the Jolly Green Giant statue and museum and got us wondering what other random roadside attractions we might be able to find. This led us to the discovery of The World’s Biggest Ball of Twine, also in Minnesota and suddenly our trip took on a whole new direction.
We decided to try and find as many random roadside attractions as we could to stop at along the way and as we soon found out, if that was our aim, then the Midwest was definitely the right place to be to find them!
Finding a couple of websites that listed this kind of thing, we began to plot our route and itinerary around these random stops! The Roadtrip America and Roadside America sites, both had useful map features pinpointing places of interest in each state and we soon had a long list for Wisconsin alone including the Jelly Belly Factory, a Cheese Castle and giant sculptures of a cow, an elephant and a bicycle!
We had a lot of debate over where our overnight stops should be in each state, how long our drive times each day could reasonably be and what routes to take and there had to be a lot of compromise. Eventually, we realised that adding in North Dakota was too much of a stretch so we dropped the 4 days we’d have spent there and in South Dakota from our original plans, leaving us with a couple of days to add in elsewhere along our route which we ended up allocating to a stop in Branson, Missouri.
A rough route worked out starting and ending in Chicago and taking exactly 3 weeks, the 2 of us who were school teachers and had more time to play with plotted out an extra week or so on the end of our trip with the aim of ticking off the states of Michigan and West Virginia and ending in Philadelphia – a city we’d made an hour’s stop in on our Trek America tours but felt we needed a bit more time exploring.
Flights booked, we went back to the first draft of our itinerary and spent the next few months fine tuning it, looking at where we’d make our one or two night stops and booking roadside motels or convenient city hotels. Here, we found a slight problem for travelling as a group of three in that most accommodations offered rooms with 2 doubles and didn’t offer triple rooms or rooms with an extra bed. This meant that most nights, two of us had to share a double bed while we took turns have the other bed to ourselves! Car parking was also something new for us to consider and while most roadside motels offered it for free, this was rarely the case in the cities so we had to factor this into our budget.
We had originally said we’d aim to keep drive days down to a maximum of 4-5 hours driving but the more we researched the states we were passing through, the more random roadside attractions we found that were ‘just a short diversion off our route’ and just had to be added into our itinerary. We even managed to alter our route to include cutting through a corner of Texas as one of us hadn’t been to that state before!
Suddenly, we found that some of our 4 hour drive days, were now 6 or 7 hour drive days but we told ourselves it would be fine as we could make an early start and share the driving three ways. With two of us making it clear from the start we were much less confident with city driving, we also had to make plans to switch drivers well before we reached any cities on our itinerary.
The last thing we got around to booking were the attractions and activities that needed to be booked in advance. Where possible, we booked these in places where we were staying 2 nights so we were already in the area and didn’t have to factor in possible traffic stopping us from reaching the attraction on time. If we couldn’t do this, then we aimed to book them for first thing in the morning on the day we left that area so any driving was after. There were a couple of activities including ziplining in Kentucky where we had to book for the afternoon we arrived so we made sure we didn’t have any other stops planned along the way that day and added an extra hour or so onto our arrival time, booking a slot for late afternoon. It was good job we did in Kentucky as we had completely forgot to factor in US time zones into our plans and we later realised we would lose an hour crossing a time zone that day!
There were also some activities we had to drop purely because we didn’t have the time – we’d read that in Nebraska, something called ‘tanking’ was a popular summertime activity. It involved floating down a river sat in a giant tub and it looked like great fun. But as we researched it, we realised it was a full day activity with tanking trips taking 4-5 hours and unfortunately there was no way we could fit that in. We replaced it with an air-boating trip on the River Platte so we did at least get out on the eater!
When our trip finally came around, we were very excited but also nervous at the thought of hiring a car and driving around such a huge country, on the other side of the road, with its complicated multilane highways around the cities. We had a great few days in Chicago after arriving in the US but sat in silence on the subway en route to the airport to pick up our hire car on the day our road trip was to begin, probably all thinking about all the things that could go wrong!
Three weeks later, we were back in Chicago after what had been, all in all, a pretty successful trip. While we had learnt that we had way over planned what we could fit in on a drive day, we had made it to many of the roadside stops we had in our itinerary and had made it on time to all of the activities we had booked specific time slots for along the way. We also found out that 6-7 hours drive days were not a good idea as we somehow seemed to add on 3 hours to the timings we had down in our itinerary each day once food stops, petrol stops, stops to switch drivers, time spent at each attraction along the way and general faffing had been added in; so an estimated 4-hour drive day took us 7 hours and a 7-hour drive day took us 10 hours!
Lessons learnt for our next US roadtrip and there have been 2 more equally successful trips since.
I’ll be writing about our trip soon so come back to find out exactly how our trip went and what we got up to along the way soon!!
Miss Travels 
14 thoughts on “Planning a US Road Trip”