Hidden Gems and Open Roads: The Most Underrated Adventure Through Midwest America

In 2017, I embarked on a transformative 2-week road trip throughout the Midwest, which became one of the most life-changing and affordable journeys I’ve ever experienced. The Midwest, often overlooked in favor of popular destinations like New York, Los Angeles, Austin, San Francisco, or Denver, holds a significant place in American culture and history. This trip was particularly profound for me, as it provided a much-needed opportunity to sit in silence and reflect.

I decided to take this trip primarily to visit my grandpa, whose health was beginning to decline. I wanted to spend meaningful time with him while he still had his memories, something I regretted not doing with my Granny before she passed away. Although I wasn’t very close to my grandparents and was distant from my parents at the time, this journey brought me closer to my family. Spending just a few days with my grandpa made me realize the complexity of family relationships and I was fortunate to gain a mature perspective on it.

The first leg of my trip took me from Austin, Texas to Fort Wayne, Indiana, where my grandpa and a few of my dad’s siblings lived. I stayed there for a few days before heading to Detroit to pick up my friend, Greer, whom I had recently met in Austin. Together, we drove back to Austin, making unforgettable memories along the way and only spending $100 each on accommodation during those 2 weeks.

This Midwest road trip was not just an exploration of new places but also a journey of self-discovery and reconnection with loved ones. Here’s the bullet points of where I went that were the main highlights:

Day 1: Driving through Texas, Arkansas & Tennessee

I still marvel at how I managed to pull this off—perhaps it was youthful energy or the sheer excitement of the journey. After a demanding five-hour shift giving massages and attending a friend’s baby shower, I embarked on a grueling 12-hour drive through a relentless storm in Arkansas, with only the haunting narration of Gone Girl to keep me company. As I reached Memphis late into the night or early morning, I vividly recall crossing the state line between Arkansas and Tennessee. Chris Isaak’s Wicked Game played just as I crossed the bridge over the Mississippi River, creating a moment of surreal solo adventure. Arriving in Memphis, I parked at a Holiday Inn and spent the night in my car—something I now find almost unthinkable at 32, given how unsafe it seems.

This trip was accompanied by a playlist that became a cherished soundtrack to my Midwest adventure, a collection of songs that holds an incredibly special place in my heart.

Day 2: Mammoth Cave National Park & Red River Gorge

The next morning, the warmth of the early sun gently stirred me awake. I brushed my teeth in the Holiday Inn parking lot and prepared myself for another long day on the road. My first destination was Mammoth Cave National Park, a five-hour drive away. Nestled in Kentucky, Mammoth Cave is the longest cave system known to man, with 426 miles of passages discovered. Now that I live in Northern Alabama, my fascination with cave systems has now deepened, and I look forward to exploring and writing more about these hidden wonders in the future.


With a long day ahead, I didn’t linger too long at Mammoth Cave and continued my journey towards the Red River Gorge, which was a 3.5-hour drive away. The route was dotted with numerous bourbon distilleries, adding a unique touch to the scenic drive. Known for its excellent rock climbing opportunities, I went for a short hike and ended up befriending some climbers. To my surprise, I met a couple from India who had traveled all the way to Kentucky for their rock climbing adventure. My naive self at the time couldn’t quite grasp why anyone would journey across the globe for this destination. Nonetheless, it was a pleasure sharing dinner with them. Now that I’m living much closer to Red River Gorge than I was in Texas, I look forward to returning and exploring it further. This is definitely a place I’d like to spend more time and revisit.

After another 3 hours on the road, I set my sights on Hocking Hills State Park in southern Ohio. Even though darkness had settled in, the atmosphere of Ohio was palpable—the change from Kentucky architecture and the growing presence of cornfields set the scene. The night had an eerie quality, heightened by the fact that I had been binge-watching Stranger Things, which had just released its first season that summer. With the show’s setting in Indiana and Ohio as a neighboring state, the midwestern eeriness seemed to resonate even more. I recall the full moon casting an eerie glow through the cloudy sky, adding to the spooky ambiance. The crisp breeze hinted at the onset of fall, a welcome change from the August heat I was used to in Texas.

Unfortunately, my lack of planning became apparent when I discovered that every campsite in Hocking Hills State Park was fully booked. Exhausted, I decided to pull into a random parking lot and sleep in my car. As I was drifting off, a sudden knock on my window jolted me awake, sending a surge of fear through me. It was a female sheriff who, to my surprise, bore a resemblance to Sheriff Jim Hopper from Stranger Things, amplifying the Ohio eeriness. She informed me that I couldn’t sleep there and that if I were found outside my car, I could be arrested—a word that instantly snapped me to attention. However, she kindly directed me to a nearby truck stop and bathroom facility just five minutes away, where I could safely rest for the night.

Day 3: Hocking Hills State Park & Cleveland, Ohio

The next morning, I woke up refreshed and took the opportunity to explore the stunning Hocking Hills State Park. It was another gem of the Midwest that I’d love to revisit. This trip offered me glimpses into the hidden beauty of the region—scenes that are often overlooked or kept away from the spotlight. Hocking Hills revealed its charm through its dramatic cliffs, cascading waterfalls, and serene, forested ravines. Each corner of the park seemed to hold a secret, showcasing the enchanting landscapes that make this part of the Midwest so special.

Screenshot

My next destination was Cleveland, where my Aunt Barbara and Aunt Nancy live. To maximize my time with them, I didn’t spend too much time in Hocking Hills State Park. Unfortunately, I didn’t get a chance to see Aunt Nancy, but I had a wonderful evening with Aunt Barbara. It had been seven years since our last visit, and it would be another six years before I saw her again, which was this past winter (2023). Our dinner together was truly refreshing; catching up with her as an adult was a different experience from when I last saw her as a teenager. We enjoyed some karaoke and had heartfelt conversations about the joys and challenges of life. With two sons of her own, I could tell she appreciated the opportunity for one-on-one time with her niece. Although I wished I had planned more time for our visit, I made the most of the evening we had together, cherishing every moment of our reunion.


Day 4-7: Ft. Wayne, Indiana

During my time in Fort Wayne, I didn’t do much sightseeing; instead, I focused on spending quality time with my grandpa, Uncle Brian, Uncle Don, and Aunt Louise. Our reunion was truly special. We spent hours talking and catching up, and I introduced them to the game Cards Against Humanity, which sparked a lot of laughter—especially since they had never played it before. I also gave my uncle a Thai massage, a modality that I specialized in at the time, and it was his first massage ever, which he was certainly overdue for!

My family has struggled to part with anything that belonged to my Granny. Even her last Miller Lite was still in the fridge (for two years), and they graciously let me have it. Drinking that beer felt like a tribute to her memory. Additionally, sharing an Old Fashioned with my grandpa was a meaningful moment. It wasn’t about getting intoxicated but about experiencing something special together.

Screenshot

Day 8: Detroit, Michigan and the Upper Peninsula

Writing about this day brings a wave of emotion, as it marked both the continuation of my journey and a bittersweet goodbye. I vividly remember seeing my grandpa asleep in his favorite recliner, a mustard stain from dinner the night before still on his shirt. It was time to wake him, but I knew it was a moment tinged with finality. Gently, I touched his shoulder, and when he opened his eyes, we locked gazes, a profound silence spoke volumes. In that moment, we both understood that it would be our last meeting.

The embrace that followed was heavy with meaning. Unlike casual farewells where we might think, “I’ll see you again someday,” this was a goodbye without any illusions of future encounters. That last embrace remains etched in my memory, a reminder to cherish every moment with others as if it were our final one. Having glimpsed the afterlife myself, I carry that awareness deeply, though I know I still sometimes take life’s precious moments for granted. One day, I hope to write about my Near Death Experience, a task that feels far more daunting than recounting travel adventures. I drove from Fort Wayne to Detroit, tears streaming for two and a half hours, grappling with the weight of that final farewell.


Upon arriving in Detroit, my next stop was the airport to pick up Greer, a friend I had recently befriended in Austin. We had met a few times through mutual friends, and after sharing my road trip plans with her at a potluck the previous week, she was intrigued and asked if she could join me halfway. I was thrilled to have a traveling companion, and we decided that Detroit would be the perfect meeting point. This trip marked the start of many more adventures together. The deep conversations and shared experiences during our drive created an exceptionally strong bond between us, making our time together truly special.

From Detroit, we continued north towards the Upper Peninsula of Michigan, an incredibly magical place! If I had to choose only one destination to revisit from this trip, it would undoubtedly be the Upper Peninsula of Michigan. As we drove into Mackinaw City, right before crossing the bridge that connects the Lower and Upper Peninsulas, we could see both Lake Superior and Lake Huron—two of the Great Lakes. To the left was Lake Superior, and to the right was Lake Huron. The sight felt like a magical dream.

Entering the Upper Peninsula, we noticed an abundance of signs advertising ‘pasties,’ pronounced ‘pass-tees.’ I asked one of the store owners about ‘paste-ees,’ and he burst out laughing, correcting my pronunciation. We tried one of his pasties, and it was incredibly delicious.

Our destination was Pictured Rocks National Lakeshore. A bit confused by Google Maps, we parked at a random spot we found, eager to begin our hike. The sun had already set, so we started backpacking in the dark. This was Greer’s first time backpacking, and she was immediately hooked. Signs warning of bears made me a bit nervous. As we ventured into the forest, the dirt path gradually turned to sand, and the sounds of the waves from the Great Lakes crashing against the cliffs added to the surreal atmosphere. It was so dark and loud that I thought we were near the edge, which scared me a little. Eventually, we found our campsite, set up our gear, and settled down for a night’s rest.

Day 9: Pictured Rocks National Seashore

Pictured Rocks is truly incredible. I have no clue why it hasn’t been recognized as a National Park, but perhaps that’s a good thing, as it would likely be overrun with visitors due to its surreal beauty. When Greer and I woke up the next morning, we thought we would go on a short 20-minute walk, but it turned into an 8-hour hike! We were utterly unprepared, with just one water bottle and no snacks. Fortunately, the hike wasn’t too challenging, and every few minutes, we stumbled upon breathtaking views, each more stunning and unique than the last. It was hard to believe such a place existed!

We were lucky to meet kind people along the way who shared their food and water with us. One guy was barbecuing on the beach and generously fed us. At the time, I was vegan, and Greer was vegetarian, but our hunger overrode our dietary restrictions, and we gratefully ate the meat he offered. It was incredibly nourishing. Another hiker suggested we jump into Lake Superior, the coldest lake in the world. High on life, we accepted the challenge and ended up swimming in the lake, discovering secret caves along the way. We met a lovely couple who were kayaking, jumping off small cliff caves, and listening to the Guardians of the Galaxy Vol. 1 soundtrack, which added to the perfection of the moment.

Screenshot

After our unbelievable adventure, we eventually found our way back to our tent and gear, laughing at the day’s unexpected journey. Reluctantly, we knew we had pack and continue our trip. Once we got back to the car, we decided that I would drive for three hours while Greer slept in the back of my Prius. We parked at a Holiday Inn in Green Bay, Wisconsin, to rest for six hours. Greer woke up early and took over driving for another three hours to The House on the Rock in Spring Green, Wisconsin.

Day 10: The House on the Rock & Davenport, Iowa

How do I even describe The House on the Rock? It’s like the original Meow Wolf with an extreme vintage touch. Opened in 1959, it exudes the vibe of that era, making it a fascinating trip for anyone who appreciates history and historical artifacts. While Meow Wolf offers a modern, artificial, psychedelic parallel universe experience, The House on the Rock feels like stepping into a literal time warp.

During our exploration, we stumbled upon a bar, which added to the fun and made the experience even more unique. The House on the Rock is truly difficult to describe. My dad, born in 1952, visited with his family as a boy, and it was fascinating to imagine him enjoying this eccentric place in the 60s. That must have been quite the trip.

You can only imagine that Greer and I had only been together for 48 hours, but we had already embarked on quite the adventure. The next day was the total solar eclipse, and I had read that one of the best places to view it was Nashville. So, we decided to take on the 10-hour drive to ensure we didn’t miss it.

After driving for two hours from The House on the Rock, we saw a sign that said ‘Iowa this way.’ On a whim, we decided to check out Iowa and ended up in the charming town of Davenport. It was a lovely, quaint place, and I’d love to bring Adam, my fiancé, there one day. After our brief detour, we continued the long drive to Nashville.

Fortunately, one of our mutual friend’s friends let us stay at her place for the night since every place in Nashville was booked due to the eclipse. It was an incredibly kind gesture that added to the serendipitous nature of our journey.

Day 11: The Greatest Total Solar Eclipse in Nashville

Greer and I woke up well-rested, especially since this was our first actual bed since I had picked her up from the Detroit Airport. We were greeted by surprising messages on our social media. I had a message from an old friend, Justin, who I went to middle school with in San Antonio. He had been following my Facebook posts about my travels through the Midwest and guessed correctly that I would be in Nashville. He invited me to his friend’s vegan barbecue. Greer also had a message from an old friend, Reagan, from high school. He had seen her profile pop up on Bumble and, noticing she was in Nashville, messaged her on Facebook to meet up in the evening.

It had been about 13 years since I had seen Justin, and it was such a nice and spontaneous reunion in Nashville. It was really nice to meet his wife too! Justin and I used to be nemeses in our orchestra class, always competing for the first chair. We didn’t know what to expect during the total solar eclipse, but we were super excited. As the totality approached, the day sky began to darken, and the sounds of animals and insects filled the sound of the air. It was one of the most beautiful and incredible phenomena I had ever witnessed. Everyone at the barbecue was completely stunned and in awe. Ever since, I haven’t been able to stop talking about the total solar eclipse and have become mesmerized by all things space.

I’ve been fortunate to see an annular solar eclipse in Austin, TX in 2023 and another total solar eclipse in Poplar Bluff, Missouri in 2024. I have a blog specifically about those and other cool astronomical experiences here:

Later that evening, Greer and I drove over to her friend Reagan’s house, where we hung out with him and his roommate Gary. We got some drinks at The Crying Wolf, a really cool spot in East Nashville that, unfortunately, it is no longer in business.

It’s cool to think how this was my first time in Nashville and how much I enjoyed its vibe. Now that I live in Northern Alabama, visiting Nashville is such a regular thing. I never thought in my life I’d be in this position.

Day 12: City Museum and St. Louis, MO

We left early in the morning to head towards Missouri. Although it was out of our way back to Texas, we wanted to check out the City Museum in St. Louis. After a 5-hour drive, we arrived at this incredible all-ages playground housed in a 12-story old shoe factory. The converted space, located in downtown St. Louis, was filled with tunnels, caves, slides, and rides both inside and out. Even if you don’t have kids, I still recommend this place, which also has hidden bars in the building!

After our fun excursion, we explored a bit of downtown St. Louis, checking out the Old CourtHouse, the Gateway Arch National Park, and the Cathedral Basilica of St. Louis. Once we were ready to settle in for the night, we drove to our Airbnb, which was essentially staying on someone’s land and setting up our tent for $40. We were in Portage Des Sioux, Missouri, right off the Mississippi River, with a view of Illinois across the water.

The couple that let us stay there asked if we liked catfish and if we wanted to join them for dinner. While they went fishing, we borrowed their paddleboards. It was my first time paddleboarding, and we had a lot of fun exploring this part of the Mississippi River until Greer accidentally fell off her paddleboard and ended up in the mud. There was a shower inside a red phone booth, which was pretty quirky and cool. Once we were refreshed from our paddleboarding adventure, the couple finished battering and frying up the catfish they caught and invited us to feast with them. It was such a fun and incredible time!

If you’re interested in pitching your tent or even staying at one of their Campers/RVs, you can find it HERE.

Day 13: Eureka Springs, AK

Greer and I decided to check out the St Louis Farmer’s Market which was a bit anti-climatic since it was early in the morning and not on the weekend. But I could imagine it on the weekend, and would love to come back and experience that vibe. We bought some of the most delicious cherry tomatoes from a farmer who recommend us to stop by Lambert’s Cafe which was on our way to Eureka Springs. So off we went to Lambert’s Cafe, in Ozark, MO, home of the “throwed rolls”.


As we finally crossed from Missouri into Arkansas, the landscape unfolded into the breathtaking beauty of the Ozarks in full summer bloom. I had visited the area once before, back in the fall of 2015, and while the autumn colors were unforgettable, there was something about the lush green of summer that made the scenery even more vibrant. If you’re curious, you can check out my previous article on The Ozarks and Eureka Springs for more details here:

Greer and I eventually arrived at our Airbnb, the same cozy spot I had stayed in during my last visit. I had such a wonderful experience back then that I couldn’t resist returning. However, this time, the hot tub—one of my favorite features—was sadly out of commission. But despite that small disappointment, the trip was going splendidly.

As the end of our getaway loomed closer, we decided to venture into town for a few drinks. There, we encountered some of the most fascinating characters. First, we met Willow, a man who had taken a vow of silence and was mute. Yet, he communicated volumes through his eyes and his art. He shared with us some of the sketches he’d been working on, each one more intricate and darker than the last…

Next, we met Chris, a wind chime maker who travels to Renaissance festivals across the country, selling his handmade creations. He also dabbled in moonshine-making and offered to sell us some. The offer piqued my curiosity, so we followed him to his car, which, to our slight apprehension, turned out to be a white van. The entire situation had Greer and me exchanging glances that clearly said, “This feels sketchy.” Chris then pulled out a bottle of blueberry lemonade moonshine and insisted I taste it before buying. Though the situation seemed dubious, I cautiously pretended to try it, thinking I might end up drugged, but everything turned out just fine. As it happens, the moonshine was incredibly good—some of the best I’ve ever had, and I’m not even a fan of straight liquor!

Later that evening, we decided to check out another bar nearby, which was located just off some rainbow-colored staircases. We chatted with a few locals, but there was one man I’ll never forget. He looked exactly like John Malkovich—so much so that I wouldn’t have been surprised if it had actually been him. He enthusiastically talked about his passion for making dollhouses and even showed me his pinky nail, which he used for painting the tiniest details on his miniatures. While I admired his dedication to his craft, the whole thing was a bit unnerving, and we decided it was time to head out.

Exhausted from our day, we ended the night by eating leftovers from Lambert’s Cafe and watching the season finale of Game of Thrones Season 7, before drifting off to sleep, the memories of our quirky adventure still fresh in our minds.

Day 14: Dallas, TX

The miles between Eureka Springs and Dallas seemed to stretch longer than they actually were. It was a bittersweet drive, knowing that our adventure was nearing its end. What started as a journey with someone I barely knew had evolved into something far more meaningful. Greer and I had gone from acquaintances to friends who now shared a bond forged by the countless memories we’d made along the way.

The Dallas skyline eventually came into view, signaling the final leg of our trip. We arrived to visit Greer’s sister and took a brief tour of Greer’s hometown. It was cool to see where she grew up, adding another layer to our friendship.

All the while, Hurricane Harvey loomed ominously over the Texas coast, a reminder that our road trip was ending just as a new, unpredictable chapter was beginning for those in the storm’s path. As we navigated the final stretch, I couldn’t help but reflect on the incredible time I’d had, not just exploring new places but also discovering a deeper connection with someone I hadn’t expected to bond with so closely.

Day 15: Back home to Austin, TX

As we made our way back to Austin, the familiar roads brought with them a mix of emotions. Austin was home for both of us, but after everything we had experienced, it felt different—like returning with a new perspective, a deeper appreciation for the life we were stepping back into. I had to head straight to work that evening, and the next day I was moving, only to jet off to Tulum for a wedding a few days later. My Midwest adventure was coming to an end, but my week was still brimming with new experiences on the horizon.

Reflecting on this time, seven years later, fills me with immense gratitude. This road trip, this newfound friendship, and the stunning beauty of the country we explored have left a lasting mark on my heart. I never imagined that one of the best road trips of my life would take me through the Midwest—a region often overlooked, where the quiet, unspoken charm of small towns and open roads revealed something extraordinary.

There’s something special about the places that aren’t in the spotlight, those hidden gems that don’t make the headlines but offer so much if you take the time to discover them. This journey was filled with peace and serenity, a kind of magic that you can’t find in more crowded, bustling destinations. I’ll never forget the summer of 2017, a season that brought me closer to family and the Midwest’s subtle wonders. It was truly an underrated adventure, one that will forever remain a cherished memory in the story of my life.