A 14 Day Midwest Road Trip [ Day by Day + Map]

Sometime during 2018, I set a goal to visit all 50 states by the time I was 30. At that point, I was 27 and had some time. I had already visited about 36 states, so it shouldn’t be too hard to visit the last 14 or so that were easy to drive to.

I was headed to PA for a wedding on a Saturday in October, so rather than return to Tampa to then fly to the somewhere to begin a road trip, I decided to leave from PA. I initially planned to travel for about 2 weeks by myself, but my dad mentioned he was interested in joining me for “the cool parts”, so he spent the first week with me before I dropped him off at the airport in Kansas City, MO at our halfway point.

I planned where I wanted to go on this trip ahead of time, but not exactly when I to visit. I had only booked hotels for the first 2 nights. The others were booked the day prior, or hours prior to us arriving. The map below is an incredibly general route of where we went. Google Maps would only let me enter in so many destinations, so there’s a lot missing.

The entire trip was about 4500 miles and I did about 65 or so hours of driving in 11 days.

Day 1 – Monday

  • Dad and I had an early flight from Harrisburg, PA to Madison, WI.
  • It was early October so the leaves were already starting to change in the northern states. Madison’s trees were very fall and it was gorgeous to walk the sidewalks and see all of the leaves changing.
  • From Madison, we headed west through the area of Wisconsin Dells. An interesting place.
  • We stopped at the roadside attraction of the Cheese Chalet and stocked up on various cheeses for the few hours we had ahead of us.
  • We drove through Wisconsin stopped for dinner in Eau Claire at the District Pub and Grill and dined on cheese curds.
  • Our hotel was in St. Cloud, MN so we continued on for a few hours to check in and head to bed.

Day 2 – Tuesday

  • We got up around 8 and it was only 44 degrees out. We both had packed warm clothing, but not cold winter clothing. Layering was now a necessity.
  • We ate breakfast at at Brigitte’s Cafe with the regulars (who were all retired of course) and enjoyed our eggs and pancakes and home fries.
  • Next stop was Munsinger Gardens in Saint Cloud. It was along the water and was free to visit. We walked through the various gardens enjoyed the fall scenery along the water.
  • We stopped in Alexandria, MN so Dad could visit Fleet Farm – a farm supply superstore. Think Walmart meets Cabelas meets Home Depot. Dad was in heaven.
  • While he was shopping for things he couldn’t even haul home, I walked across the street to the coffee shop, Dunn Brothers Coffee to get some caffeine. Then we headed to lunch at Dolittle’s Woodfire Grill.
  • We continued on our way to North Dakota State University in Fargo. The downtown has a variety of shops so we walked in a few and got snacks at Atomic Coffee and some warmer clothing for the upcoming days in the Dakotas.
  • We looked online at places on our route to the hotel for dinner and ended up in Jamestown, ND at Sabir’s Buffalo Grill. We spent the dinner looking at the register of historical places in the city. It was a riveting conversation.
  • Stay for the night was in Bismarck, ND. We were tired after 400 miles of driving and about 6 hours in the car.

Day 3 – Wednesday

  • We were up around 7 AM, but the sun was not. At 7:30, it was still pitch black outside.
  • We drove outside Bismarck to Mandan and the Fort Abraham Lincoln State Park. There’s a Slant Indian Village that was occupied by the Mandan Indian Tribe between 1650 and 1750.
  • Next stop was Theodore Roosevelt National Park. This was the first time we’d see snow on the trip but wouldn’t be the last. We drove the scenic route in the park and all we really wanted to see was Bison. We searched high and low for the bison that are known to be there. With only 10 minutes or so left in our 90 minute drive, we spotted one. He was on his own away from the herd. We turned the car around and got out on foot to spot him. He was in a valley and we were on the ridge, but we found him. I got spurs through my shoes but it was worth it. We spotted him.
  • I highly recommend this park. The scenery is beautiful, there’s not much traffic at all, and wild horses, bison, pheasants, and many other animals.
  • We drove into Medora for lunch and ate at Boot’s Bar and Grill. Since we were there during the off season, there were not many people around which is fine by us!
  • To get to South Dakota, we detoured into Montana for a bit. I couldn’t believe just how blue the skies were and just how flat the terrain was. I actually felt like I was in a picture.
  • Dinner was in Spearfish at Steerfish Steak and Smoke. We tried a few different dishes but it was all delicious.
  • Rapid City was our home for the night before exploring more of SD the next day.

Day 4 – Thursday

  • First stop – caffeine at Dixon. A little tiny house looking business in the middle of a parking lot.
  • If you’ve ever driven across Route 90 in South Dakota, you will have seen upwards of 100 billboards for Wall Drug. I had no idea what it was before the billboards, but after seeing so many, you really don’t have a choice but to stop.
  • Dad and I stopped in the town of Wall. The town itself has a population of about 800 people. Wall was established around 1907 as a railroad station. From there, it got postal service, and more people moved to the area. Now, the town of wall looks to be made up of blocks and blocks of the Wall Drug Store. Don’t let the name fool you. It has a bookstore, a chapel, leather goods, a cafe, ice cream, trinkets, toys, and so much more. It is literally blocks long.
  • Dad and I got breakfast sandwiches and coffee here. (I learned it’s a thing to put jelly on your breakfast sandwich. This was news to me). After getting our fill in Wall, we were headed to the Badlands.
  • The Badlands cover 240,000 acres of land. The road you enter is called a loop but route 240 will but will take you in one side of the park and out the other side. There’s hiking trails and scenic vistas you can stop at along the way. Since Wall Drug is so well known for their donuts, Dad and I stopped and got some and had a donut picnic at one of the pull offs in the park. This is another one of those places where the pictures just don’t do it justice. Everywhere you look was blue sky and wide open spaces.
  • From the Badlands, we drove towardDuluth Trading Company which was Dad’s request in Sioux Falls, SD.
  • We had dinner at Crawford’s Bar and Grill and it was incredible. I got a steak salad and then we walked down the street and picked up some macaroons for dessert.
  • We drove a bit to our hotel which was in Sioux City, Iowa before it was time for lights out.

Day 5 – Friday

  • Friday was a hazy morning as we drove through Iowa. We were headed to Council Bluffs where the Union Pacific Railroad Museum is located. (P.S. I love trains)
  • We spent some time in the museum learning about the history of the railroad and more about the Transcontinental Railroad (my favorite thing to learn about train related).
  • Form there we headed to Omaha Nebraska to the Lauritzen Gardens and then downtown for lunch.
  • We had lunch at the twisted fork and has these wonderful brussel sprouts. The fact Dad ate them, let alone liked them was a miracle. He’s not a “green food” fan.
  • Next up was Lincoln, Nebraska. We walked around the city and to the capital building. Did you know there’s a Lancaster County in Nebraska?
  • Our hotel for the evening was to be a chain hotel in Hiawatha, Kansas. We planned to get dinner before checking in, and I’m glad we did.
  • We ended up at The Country Cabins in Hiawatha for dinner. It wasn’t just a restaurant, but really did have cabins and happened to have one free for the evening. We ditched our previously planned hotel and picked up the key for a cabin by the lake. It was warm and cozy and such a fun detour.

Day 6 – Saturday

  • The only snag was hit at the cabins, was for breakfast the next morning. Dad couldn’t find a plate, so he heated up a cinnamon bun in a coffee filter. He said it tasted fine, but it looked gross.
  • We headed out and got to St. Joseph, Missouri. We parked to talk around, and ended up in the middle of a parade. We found a cafe where you could eat inside, but watch the parade through the glass windows, so we hung out there for about an hour enjoying the local festivities.
  • As we walked the of St. Joseph, there were so many different wall murals to enjoy. I included a few of them below.
  • The Pony Express Museum was our next destination. It’s also in St. Joseph’s in another part of town. There was a fall festival happening so we got to enjoy both the museum and the fall activities on the neighboring blocks. The Pony Express was trained horseback riders who worked in a relay type system to carry saddlebacks of mail from St. Joseph’s to Sacramento, CA. It took about 10 days to deliver mail with this new system which was fast compared to transport in the past. In 1860, they delivered word of Abe Lincoln’s election in only 5 days. The Pony Express only lasted for a few years, as it was replaced by the telegraph system.
  • Similar to St. Joseph, Topeka, Kansas also had many painted wall murals in their downtown. Dad and I stopped downtown for lunch at Norsemen Brewing Company and enjoyed pulled pork and mac and cheese.
  • From there, we were headed to Kansas City. Dad had been in KC a few months prior for work, and said there was a barbecue place he was willing to wait in line for. This was shocking to me as he won’t even wait 10 minutes to be seated at a restaurant, let alone wait over an hour for somewhere in city. But we put our name in, and waited. The food at JackStack Barbeque was worth waiting for. The drinks were good, the food was incredible, and I loved the atmosphere. We had parked at the train station and walked in the railway bridge across the tracks to get there which was beautiful when lit up at night.

Day 7 – Sunday

  • Dad’s flight back to PA was mid-day on Sunday.
  • We started off the day walking downtown and he shared his knowledge with me about the way the train bridge worked.
  • I dropped him off at the airport, and then headed toward St. Louis. On my way, I stopped in St. Charles for a late lunch and walked around the town which was adorable. and right along the Missouri River.
  • I had booked my hotel the day of and ended up with one that overlooked the Arch. I checked in, and then decided to walk around the park by the arch and the waterfront. It was beautiful when lit up at night. I realized when I got there, that this was another landmark to now become a National Park.

Day 8 – Monday

  • I got up early Monday morning to walk downtown to Kaldi’s coffee by the park. I was headed for a few hours drive so picked up breakfast and coffee and made my way back to the hotel to check out.
  • I drove through parts of Missouri and into Arkansas as the day went on. I wanted to avoid paying tolls into Oklahoma so I went the “non toll” road and it was creepy and odd and dark. I really had no sense of where I was, and it felt like the town was miles from me and I was on odd back roads. I was so relieved to finally get into Broken Arrow, OK for the evening.
  • I stayed at the Stoney Creek Hotel and Conference Center and it was beautiful. I loved the decor, the breakfast, how close it was to downtown, and how clean it felt.

Day 9 – Tuesday

  • Tuesday morning started like most days with coffee and a pastry from a little place in Broken Arrow called Laurannae Baking Co.
  • From there, I headed to Fort Smith Historical Site. I learned that Choctaw Chief Allen Wright suggested the term “Oklahoma” for the land which combines two Choctaw words to mean “land of the red man”.
  • The line on the sidewalk you see below shows the 1834 boundary between Indian territory and Arkansas. Indian Territory was unsettled land that was west of the Mississippi river that didn’t include any previously organized states or territories.
  • After learning about Fort Smith, I went downtown to Fort Smith Coffee. The inside of the building I swooned over and still am looking back at these photos. Seriously, click the link and check them out. The blue speaks to my heart as does the wood and industrial decor.
  • While I was in line for coffee, a gentleman asked me if I had attended Temple. I had forgotten I was wearing my temple sweatshirt and let him know that’s where I had attended. While in line, we ended up talking and after I got my coffee, we continued our chat for about 40 minutes on where he was from, his family, his jobs, what he does now, and his lessons from life. I don’t share that I am traveling alone, but after talking to him for a while in a public place, felt okay in sharing that. He had gone to Oxford, MS and was able to share with me tips for where to stay and what to see while I was there. I mention this in a previous post, but sometimes the best way to “make a friend” on your trip is to wear clothing that others will recognize – often college attire is the way to go.
  • After our chat, I was headed down to the Hot Springs of Arkansas for lunch and then to Mississippi for the night.
  • My favorite chain of boutique hotels are the Graduate Hotels. So when I am on trips, I try to see if there are any nearby my destinations so I can stay there. I lucked out and they have one in Oxford. It was and still is one of my top 5 favorite hotels to date. Their interior is designed to have a local flavor and each hotel and room is unique. I got a great deal on it since I booked it the day of travel. If you take a close look at the photos below, you’ll see the interior and the “college” vibe (the Graduate, get it?). They usually have a restaurant, bar, and coffee shop all at the hotel for guests. Each hotel is near a college and the chain is continuing to grow. I’ve been to 2 so far, but really hope to visit more during my future travels.

Day 10 – Wednesday

  • I woke up and grabbed breakfast (with jelly again) and some coffee at the shop in the Graduate Hotel and then spent some time at the long table below working on my laptop.
  • Today’s route was going to take me east and then south, back toward Tampa.
  • I had lunch in Huntsville, Alabama at Farm Burger. The vibe was cool and the burger was really good.
  • I drove around the city a bit and then headed for Amicalola Lodge in northern GA. This lodge is on top of a mountain, so if you’re car isn’t in the best shape, it may not make it. The view from the deck of the lodge and the mountain facing rooms is unreal. I spent an hour or two outside freezing just to enjoy watching the sunset over the mountains. I actually ended up loving the lodge so much that I will be spending an evening back about two months after writing this post.
  • They have a restaurant at the lodge were it’s a buffet style. I decided to just eat there rather than leaving down the mountain and having to come back up in the dark. I met some wonderful people from England who were traveling for a few weeks in the US. We got to chat about where they’re from and where my grandmother is from (Torquay). I don’t always talk to people during meals, but it was nice to chat and learn more about their trip in the US.

Day 11 – Thursday

  • This became my last day of the road trip. When I initially booked it, I planned to come home anywhere from Thursday – Sunday depending on my energy and what I wanted to see. I was ready to go back to a routine that didn’t include 8 hours of driving every day.
  • I got up and did the hike from the top of the falls down about half way. Since it was October during my visit, the leaves were still pretty green, but were beginning to change. The steps along the falls are not for the faint of heart. As you can see in the photos below, I started with a sweatshirt on since it was crisp, but ended up in a tank top because the stairs were killer.
  • After checking out of the lodge, I drove the hours south back to Tampa. I passed a few small towns that were worth stopping in, but eventually made it back to Tampa late into the night.

At the time I took this trip, this was the first time I’d gone on a road trip for about a week with someone else. I wasn’t sure what to expect, but spending that week with my dad is one of my favorite memories of the two of us together. We had lots of laughter, an appreciation for the outdoors and the wide open spaces, and both were quite interested in having a bison sighting. Anyone who’s willing to put up with my ridiculousness to find bison is a real winner.

As you also saw from the pictures, my dad and I did more fun things together than I did on my own. As I was writing this post, I was shocked by the 40 or so pictures we would have in the Dakotas, whereas during the days on my own I’d have about half that.

On this trip, I visited many new states. The last one to round out my lower 48 was Alabama. I may have shed a tear when driving into the state (which I’m sure is not normal. I mean, it’s Alabama ) but it made me grateful for surviving and enjoying my road trip from north to south. While I may not be able to take a trip like this every year, I’d love to take one as close to yearly as I can with my dad as long as he’s up for it. This “Last of the 48” will forever be one of my most cherished trips.

Leave a Reply