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The Upper Midwest: A Road Trip for 2021 - Part I

Updated: Sep 27, 2022

"Not all who wander are lost."

- J.R.R. Tolkien

Each year I try to make two or three road trips, even if they are limited to a few days. In 2021, I struggled to make that happen. I was pushing up against an exceptionally demanding work life that left me little time to plan road trips, let alone take them. I was able to accommodate just one extended road trip that year -- a two-week driving tour of the Upper Midwest with a starting point in Omaha. The time away would do me good -- there would be ample time to decompress and untangle those work-related stress knots. I had another goal in mind, though. I planned to continue my quest to visit more new counties, mark five more states as being "completed," and advance my total county count further toward the finish line. Before the start of my road trip, I had visited 1,935 counties (~61.5% of the U.S. total) and had finished 17 states. With two weeks planned on the road, I could really move the needle on those totals.

In this article, I’ll share some of my favorite places that were part of this road trip experience.

(Photo was taken on August 1, 2021 along Highway 15 just south of Wayne, NE.)


July 31, 2021 - Saturday

The first day of vacation is often the best one — the day when everything is still in front of you and you are filled with the excitement and anticipation of the journey. That's how I felt when my flight arrived in Omaha that day. I could hardly wait to get off the plane. Buzzing with the electric energy of anticipation, I practically sprinted through the airport on my way to pick up my rental car. That high octane feeling lasted until I got to the Thrifty Car rental desk. Coming to Omaha, I knew I would be paying a premium for my rental car. I had reserved it more than three months before, and even with that much lead time, I was still on the hook for more than $1,300. And I was not alone. With rental car fleet reductions not yet replenished from the year before, everyone was paying double or triple the normal rates, and happy to do so just to have a car. This is the part of the car rental story I was prepared for.

The real shock came when the rental agreement was presented to me, and in a maneuver I had never witnessed before, I was asked to sign a clause in which I promised not to take the car out of Nebraska, or any of its neighboring states. I had never been limited by contract where I could drive. The news was jarring — I had already meticulously planned out my road trip, and it would not be limited to Nebraska or its neighboring states. I had planned to sweep up the remaining unvisited counties in five states, two of which were outside the boundaries defined by the rental agreement. I had already made reservations at hotels across the Upper Midwest, and had prepaid for some. If I were forced to mind the letter of the agreement, I would have no choice but to redesign my entire two-week adventure, cancel hotel reservations, likely lose deposits, and resign myself to a less interesting road trip experience that was far more "local" than I wanted it to be. The penalty for leaving the defined travel area was $500. I had an agonizing decision to make -- play it safe and not risk the penalty, i.e., live with the massive inconvenience of forfeiting plans that were months in the making, or say to hell with it and stick with my original plans -- go to those places I had already planned to visit -- and gamble on there not being a GPS tracking system in my rental car. (As a side note, the neighboring states defined in the agreement did not include Wyoming, which borders Nebraska on the west, but did include Minnesota, which shares no state border.)

After two days on the road, I decided that a potential $500 penalty was not as important as pursuing the experiences I had previously planned on. I would just consider it another cost associated with travel.

With my rental car now secured, I left the airport and headed to my hotel downtown (Fairfield Inn & Suites at 15th and Nicholas). I definitely recommend this hotel for all you Omaha-bound travelers -- it is very clean and modern and close to the city center. After checking in and leaving my bags in the room, I headed back out to find dinner in the Old Market area of downtown Omaha. The Old Market is a historic section of the city encompassing approximately ten square blocks and sandwiched between the central business district and the Missouri River. The area is on the National Register of Historic Places and retains a turn-of-the-20th-century flavor with its streets paved in brick and horse-drawn carriages. There are lots of great restaurants, breweries, boutiques, gift shops and retail stores that occupy the many beautifully preserved buildings lining the streets. The virtual heart of the Old Market is the corner of 11th and Howard. That Saturday, in the early evening air, the sidewalks were clotted with shoppers, diners and people out for a stroll. I wound up having an amazing steak Caesar salad at the Upstream Brewing Company. Afterwards, I explored the side streets and businesses and picked up a few souvenirs.


One week later, the Old Market made national news when a flash flood tore through its streets damaging vehicles and depositing mud everywhere, in basements and in street-level parking facilities. Fortunately, no one was injured.

August 1, 2021 - Sunday

For my first full-day on the road, the goal I set for myself was to get from Omaha to Rapid City, South Dakota over a 584-mile winding journey. To make sure I could get there before sundown, I was on the road just as dawn was breaking. The weather could not have been better. The skies were clear, and the air was warm, even in the early morning. My journey took me northwest out of Omaha along US 275, then north on SR 15. It was somewhere along this route, just south of Wayne, NE, where I snapped the photo featured at the top of this article of a barn amidst the cornfields. By 10 a.m., I had crossed the Missouri River into South Dakota where Nebraska Route 15 turns into S.D. Route 19. Eventually, I made my way to SR 44 heading west through the southern tier of the state. The topography from Omaha to the start or SR 44 was dominated by expansive tracts of relatively flat farmland, broken only by the small towns with their soaring water towers every 15 miles or so. Soon enough, as my travel progressed westward on SR 44, the flatter landscape gave way to gently undulating fields and the appearance of low-lying hills and peaks on the western horizon. It was along this route where I was able to get these stunning photos of the Missouri River valley.


All along my drive that day, I passed field after field of mature, brilliant sunflowers without stopping for a photo. Shortly after crossing the Missouri River, I finally decided to pause to get a snapshot.


As I was leaving the town of Martin, SD, I noticed an orange sign on the side of the highway warning that through traffic was only permitted for Pine Ridge residents. I panicked a little. I needed to get through Pine Ridge in order to get to Rapid City without having to take an hours-long detour. I decided to drive on and take a chance that I might be let through. When I got to the Oglala Lakota County line (home of the Pine Ridge Reservation), there were two men waiting at a vehicle checkpoint. They approached my car with a clipboard and asked me where I was going, where I was coming from and what my first name was. They also asked me if I had any symptoms of COVID. When I told them I was fully vaccinated, they let me through.

The pathway to Rapid City I had originally planned was superseded by a last-minute suggestion from my iPhone. Siri recommended taking BIA 27 through Wounded Knee and a corner of Badlands National Park. Intrigued, I had never visited Wounded Knee before -- the site of the 1890 massacre. It was just a few miles north on the highway from US 18. There were no obvious memorials when I got there -- no interpretive center or marker -- just a wayside parking area and a large red sign with an abbreviated account of what happened there 130 years ago engraved on both sides.


The air was still and quiet and I felt a somberness about the place. I was the only person there. Suddenly, I heard a small voice beckon me from below the sign, down the embankment, about 50 feet away. It was a Native American woman seated under a tent, behind a table topped with handcrafted items. I went down to see what she was selling. The table was sparsely laid out with a few necklaces, some bracelets, a few bundles of dried herbs and four dream catchers. I bought one of the dream catchers which I hung from the rear-view mirror of my rental car so that I could enjoy it for the next two weeks.

At the north end of BIA 27, I entered Badlands National Park. The scenery changed quite dramatically. I was able to stop and get a few photos along the highway, but as the badlands unfolded, and I was surrounded by the stereoscopic wonder of an other-worldly landscape, I was unable to pause for photos. The road was narrow with no shoulder and a car was always directly behind me. By the time I was able to pull over, the scenery had passed. While it lasted, it was absolutely breathtaking. This was the only photo I was able to get on that stretch of road:


As BIA 27 was about to connect with SR 44, I noticed a collection of old, abandoned Wild West-style buildings alongside the highway. I stopped for a photo or two.


I arrived in Rapid City at around 5 and checked into the Fairfield Inn & Suites. During that time of year, the hotels in Rapid City can be expensive and near capacity with their proximity to Mount Rushmore and all of the attractions in the nearby Black Hills area. I would definitely recommend this hotel if you are planning a stay in Rapid City -- my room was more than comfortable, there is a free breakfast, and it is located right off Interstate 90. There is also a Perkins restaurant attached to the hotel, but access is from the outside of the building. The night I was there, the restaurant was severely understaffed with just one waitperson serving everyone, so service was slow, but I believe this was a reflection of the nation-wide shortage of service workers in general as I found wait times in restaurants to be longer just about everywhere.

August 2, 2021 - Monday

The agenda for the day was slightly more ambitious than the one from the previous day. I had planned to drive to Jamestown, North Dakota by nightfall over a 603-mile winding route designed to pick up unvisited counties that were leftovers from years of past road trips. This was a clean-up operation.

My route started eastbound on I-90 to New Underwood, then north on the New Underwood Road for 33 miles. This road, though not technically a state or national highway, was in very good condition, and carried me through some of the most spectacular scenery in South Dakota. It was also one of the loneliest roads I have traveled. I barely saw a soul along the entire 33-mile drive. You almost get the feeling that you are alone on the planet. If you pass a farmer along some of these smaller highways and county roads in the Dakotas and in many of the surrounding states, you'll often be greeted by a friendly wave. Somewhere in the northern tier of South Dakota, along SR 73, I spotted this old, abandoned schoolhouse in a field:


A little further up the road were miles upon miles of fields like this one dotted with giant, rolled bales of hay:


As a side note, in the small town of Faith, SD, there is a gas station that still operates on the honor system -- you get your gas first, then go inside to pay. I can't imagine there are many places like that left in the United States.

Heading north on SR 73, I crossed into North Dakota at around noon on SR 49. An hour or so later, I was connecting with Interstate 94 and heading east into the Bismarck/Mandan metro area. The remainder of the day was spent picking up the seven or eight unvisited counties clustered together just east of Bismarck and south of I-94. By the time I rolled into Jamestown, and checked into the Fairfield Inn & Suites, I was completely exhausted and road weary. I could think of nothing but getting a meal and getting into bed.

August 3, 2021 - Tuesday

My goal that day was to complete a collection of counties just west and north of Jamestown and finish my day checking into the Fairfield Inn & Suites in East Grand Forks, MN. My planned route didn't offer much in the way of touristy things to see or do. I was laser-focused instead on cleaning up North Dakota and quickly placing it into the "done" column. I did spot this cool-looking church on a hill along SR 200. Because it was situated on the only raised piece of land for ten miles or so, it stood out along the horizon long before I arrived:


Once I crossed into Minnesota, I decided to swing widely into the state to visit Thief River Falls and pick up the surrounding counties on the way. When I got to Red Lake Falls, MN, I stopped to get these photos of the Red Lake County Courthouse and the Red Lake River from Bridge Street:


At the end of the day, after checking into my room and marking up my map, reviewing the new counties I had passed through, I noticed a horrible blunder. I had missed a county on my way through North Dakota that afternoon — Eddy County. If I couldn’t mark that as completed, I wouldn’t be able to mark the state as completed the next day when I had planned to visit Richland County -- the last one in North Dakota. And I did not want to have to return to North Dakota someday to pick up a single county. So I checked the map, found the quickest route there and made the decision to just bite the bullet and go. It actually only took me about 90 minutes to get there, plus the 90 minutes in transit to return to East Grand Forks.


I was compelled to pull over to get a picture of this lazy creek passing through a grassy swale just east of the Eddy County line:


Back in East Grand Forks, I headed downtown where there are a number of nice restaurants along the Riverwalk facing Grand Forks, ND. I settled on a Thai restaurant called Little Bangkok where I ordered the grilled salmon with vegetables and green curry. It was amazing.


The Challenge of Sticking to a Keto Diet on Vacation

More than a month prior to the start of this road trip, I started the keto diet. My goal was to shed 30 pounds, no matter how long it took. By the time I arrived in Omaha, I was already about ten pounds lighter, and I needed to keep the momentum going. I knew it was going to be a challenge to stick with a strict no-carb diet when I would be on the road, passing places advertising burgers and tacos and pizza and fried chicken. One of the best things about being on a no-carb diet is that, after a while, you stop craving carbs altogether. Because of this, there was no internal struggle to make the right choice. What was a struggle for me, however, was the convenience of all that carb-rich food. I would have to find restaurants that had salads or fish or chicken breast (no breading) on the menu. As it turned out, I was able to find something that fit my diet nearly everywhere I traveled. Dinners and breakfasts were the easiest meals. Most hotels serve breakfast, and you can almost always get eggs and/or sausage and bacon. Even if they don't have these items, a couple of hard-boiled eggs and coffee work just fine. Lunches were a little trickier with so many fast-food places offering few if any low-carb or no-carb menu options. I found that the best places to find no-carb meals were either at grocery stores where they sold ready-to-eat salads or in the food marts of gas stations where you could find pepperoni sticks or packaged slices of pepperoni and cheese curds. Having nailed down a fairly predictable routine for locating carb-free meals, I was able to stick with my diet through the remainder of my road trip. Back home, I continued on the keto diet for another six weeks, and weighed in at the end 30 pounds lighter.

In the Next Installment ...

I'll pick up the road trip next week with travel to Minnesota and the headwaters of the Mississippi River, the North Shore of Lake Superior, and beyond. Until then, dear travelers, may all your journeys be safe and rich in experience!

48 views2 comments



Your travels are easy to envision, I feel like I am there with you. Thank you for the wonderful narrative.


Was so excited to see a new post! As usual, it was well written & interesting. It succeeded in opening my eyes to the beauty & adventure to be found in unexpected parts of our vast country. I love traveling with you. Thanks for the ride. Love your stories and love you. Mom Dianna

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