Midwestern + Northern US Roadtrip Summer 2025

This post is going to be describing my recent journey. It was significant because I did something that was hard and didn’t know if it would be possible. Weeks out I thought about the possibility of doing a cross country road trip, and I had grown to hate my job. I had a wedding in Kansas in late July, so I decided I would quit my job, go to Chicago to spend some time with my parents and friends, go to the wedding, buy a vehicle in Kansas, drive back to San Francisco in the vehicle through South Dakota, skate at some sick random midwestern DIYs, and get a new job once I got back to SF. I didn’t know if I’d actually be able to find the truck or have the gumption to do the trip solo. This is my rambling journey:

Table of contents

Chicago IL
Lawrence KS / Kansas City MO
Omaha NE
South Dakota
Wyoming
Nevada
California

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Chicago

I flew from San Francisco to Chicago on June 21. I love a one way flight, it is a symbol of adventure, it means you could go anywhere after that. In Chicago I spent time with my family at home and my friends at the skatepark we built together: Marshfield Courts. They’ve been doing great things there, throwing events and building cool stuff. They made two big ass banks that are fun to skate.

I got a trick no one else has landed on the brick bank – frontside heelflip:

We got up to some other random hijinks too – see if you can figure out what’s going on in this picture:

The morning after this picture was taken, my dad and I drove to Lawrence KS. My dad started the drive, and a couple hours in we switched. There was a problem with the car where we couldn’t connect to Bluetooth, so when we stopped I reset the car’s computer so we could connect, but the brakes didn’t turn on correctly. We were leaving a gas station and i ease on the brakes and nothing happens so I press harder, still nothing. I’m about to drive into oncoming traffic, I slam on them, still nothing, then the car stops suddenly. My dad looks at me like I’m an idiot, I ask him what’s going on with the brakes he says nothing. Whatever, I guess the brakes are super unresponsive, noted. I wait for traffic to let, and then merge onto the road and approach a light. Same thing happens with the brakes again, this time my dad’s pissed. He screams “What did you do??” In reference to resetting the computer. This sudden shift from an awesome father-son cross country drive into extreme disappointment and lack of trust in me transports me to being in high school and unable to get good grades, and how that affected our relationship. Our relationship completely changed once I became an engineer, he suddenly had respect and trust in me. I have a vague notion of remembering growing up without these things from my father, but experiencing it again made me feel it in my body and I had to fight back tears for around 30 minutes. I haven’t cried in years.

Lawrence / KCMO

I have a bunch of family in Lawrence, it’s a really cute midwestern town. Lawrence is where people who have dreams and are from KS/ surrounding states but don’t want to live in a suburb of KC or aren’t hardcore enough for KC live. Also random liberals from KS move here.

I did a bunch of hanging with my family, and went to my cousin’s wedding. Mom Grandpa and Nephew pictured here.

Across the street from my mom’s apartment in Lawrence is a sick ass bar called Tap Room. I met some Lawrence heads there including Georgia.

I went on a mad dash to try to find a truck. I was driving all over to auto shops, chop shops, dealerships, looking online, asking every person I met if they knew anyone selling a truck. My boy Colin found me something good online – a 2009 Mazda B2300 with 106k miles.

I went and drove it. It drove good, although it had a hanging bumper, cracked windshield, meh suspension – I did some negotiating and bought it. I was hyped – then I realized that there wasn’t a Chase in Lawrence – how was I going to pay for the truck? I hit up Georgia and she was down to drive to KCMO together. She picked me up and we went to this sick ass DIY – Harrison street diy.

I also got some good ass Kansas City BBQ. Also called Joe.

I stopped at the bank and I got the money. I went back to Lawrence the same day, took a shower, and went to my aunt’s house to pick her up. She rode with me to pick up the truck and be a witness to the sale. We signed the title, he cashed the check and it was done, I had managed to find a good deal on a truck and pull the trigger in just three days – which was the time frame I gave myself before I would just get a rental car.

The next day I got the car insured, registered, and took off to Omaha NE.

Omaha

As soon as I got into Omaha I went to James F Lynch skatepark

The quality of the park was amazing – the concrete was really well done. Maybe the best DIY I’ve ever been to. Really fun, well designed, great flow. Not that crusty though, which I was expecting from Omaha. I asked guys at the park what the skater bar in Omaha was and they told me that they don’t drink, which is telling. In a bigger city, I think people do a better job balancing drinking with the rest of their life. A lot of skaters in big cities can go to the bar have a couple drinks, not get wasted, and wake up the next day to make money and skate. In a place like Omaha if you drink, you probably do get wasted, and then you don’t skate. They directed me to “Alderman’s Bar” which is a Chicago themed bar, which again was disappointing. The best place in town is a reference to a different place that I already know? Whatever. I camped at a rest stop in the bed of my truck underneath the stars with my sleeping bag + pad, as I would for the rest of the trip.

Omaha is a good looking city. But like most smaller midwestern cities, people talk about how there isn’t anything to do.

I woke up the next morning and drove to Sioux Falls, SD.

South Dakota

I had driven through South Dakota once before, but in the middle of the night. One time in 2021 I was in Seattle and I asked myself “what the fuck am I doing here?” And I got on 90 and drove 30 hours straight back to Chicago. Now I was in Sioux Falls SD, on 90 again. Sioux Falls was alright, I checked out the falls.

I decided to keep going – it was July 3 and I was on a road trip. What would be the coolest thing to do on July 4 in South Dakota? I was thinking about maybe going to Sturgis for the motorcycle rally or catching a rodeo somewhere. I stopped at the one bar in Kadoka SD – it was a cowboy bar. Like a real cowboy bar, the patrons did rodeo stuff. I asked them what I should do and they told me about a kind of whatever rodeo happening, but it wouldn’t be happening until 3pm. They said the motorcycle rally in Sturgis would be good too, but that’s kind of scary – there’s definitely a lot of white nationalism wrapped up in that.

These two pictures highlight the sky. When you travel through these desolate areas of the US, there isn’t much to focus on. Your eyes always go to the sky – the sky in these northern states is just bigger.

I camped at another rest stop, woke up and went straight to The Badlands, the impetus for going through South Dakota.

It looks like Mars at this MF!!

Really beautiful. Hung out there for a couple hours and then kept driving. I stopped at Rapid City and realized I was super close to Mount Rushmore.. I decided to check it out.

It’s sad to think about how these guys took the country from Indians. South Dakota is one of the places where there are still a lot of Indigenous Americans, and one of the main attractions is these fools’ heads blasted into a mountain by a sculptor who was a white nationalist. Mount Rushmore is in the Black Hills, which is on unbelievably beautiful land that the Lakota people have had a long-standing land dispute with the US government over.

Wyoming

Not really sure why this is a section. I did drive through it but I didn’t really stop. I literally did stop, I camped at some rest stop, but I didn’t see anything. I debated going to Cheyenne vs Casper, and ended up deciding on Casper. By the time I got to Casper there was a gnarly thunderstorm that had a gust literally throw my truck onto the shoulder of the highway. I was shook and drove through it. I saw this rainbow.

This was the rest stop I camped at. Rest stops in the United States are wonderful. They’re non commercial, they have beautiful and tasteful architecture, and are refuges for travelers. They’re a symbol of an America that provided funding for things that didn’t boost a bottom line. They’re a symbol of an America that doesn’t exist anymore.

Nevada

I was really excited for the Nevada leg. I haven’t seen much of Nevada but I’ve been interested in it. I think of it as being culturally similar to New Mexico, another one of my favorite states. It’s famous for its gambling, its big cities are Las Vegas and Reno, gambling destinations. I was excited to see the “cowboy” side of it. I stopped in Winnemucca, NV for a rodeo – since I had missed the last one. I parked in the lot, and was wearing a white t shirt. I knew I was way out of place here – in just driving in the parking lot people were staring at me. I had an XL striped flannel with me that I grabbed since it was gonna get chilly soon. I walked up to a woman and asked her how to get tickets etc. and she looked at me in my eyes and said “Put on your jacket, act like you own the place, and walk through the entrance”. I did that exact thing and it worked.

I sat and watched all of the different rodeo events in amazement, I was a fish out of water. People were staring at me, probably thinking “who the hell is this how did he end up here?” Good question.

There were a bunch of different timed events – people were competing on time, they would race horses around obstacles. They would charge at a goat, flip the goat, and tie him up. They would chase a calf down, lasso it, and tie it up. Amazing stuff.

I camped outside Reno and woke up and continued down 80 the next morning. I would’ve liked to see more in Nevada but I was antsy to get back and didn’t really see anything good. I want to go back on some of the routes.

California

I was back in California now! So close to home. This was day five since leaving Lawrence, which meant my fourth day of sleeping outside, day four of no shower. I was ready to be inside, and be coding again, and doing the things I need to do to get a job that doesn’t make me feel like I’m wasting my life.

I took 80 to Sacramento and then I took routes back to the Bay. I drove along the Sacramento River, which was super beautiful. I haven’t seen too much of the central valley, so it was cool being over there.

I made one final stop at Walnut Creek Skatepark. One of the coolest skateparks I’ve been to, it feels like a DIY, the dimensions are all weird and you have to go fast. Really cool. Lil B filmed “I Own Swag” there.

I drove back to my place, and got a steering wheel lock. What an incredible, amazing trip!