Caleb Smith in Santa Monica

Caleb Smith is an aggressive, urban and distance skater from Des Moines, Iowa. This past winter he had some time off work and decided to make a trip and get his century title before turning 28. Between December 18th, 2017 and January 30th, 2018 he visited Denver, Peoria, Chicago, Madison, Minneapolis, St. Paul, Los Angeles, Long Beach, San Diego, and Austin. He made it a point to urban skate, visit a roller rink, check out a museum, eat at nice restaurants and drink at coffee shops in each city that he visited.

What made you want to do this trip?

I had some cities I wanted to travel to and I also had some life stuff that I had to get over. I really wanted to get my century (100-mile) title skating from Los Angeles to San Diego. In the end the trip was a complete success.

Skating through a cemetery in Des Moines, Iowa. Photo by Meghan Moorlach.

How did you plan for a multi-city trip?

The planning of this trip was a bit crazy. I just picked cities I wanted to visit and started looking at bus fares, plane and train tickets and ended up getting all of my tickets for 350 dollars.

How did you budget yourself to make sure you didn’t spend all your money too quickly?

So I wouldn’t over spend I had a friend put money into a spending account every week for me.

Did you bring your aggressive skates with you on this trip?

No, I didn’t bring my aggressive skates with me. It was kind of weird. At first I didn’t think about it, but later on in the trip I wanted to aggressive skate more. Not bringing them was a good thing, because I didn’t hurt myself before the BIG century skate.

Caleb ready for his blading adventure.

So your first stop was Denver, what was it like skating there?

I took the train there from Des Moines and spent a week in Denver skating. I was really lucky that the weather was good. I did a lot of solo trail skating. There is a trail that went all the way from where I was staying into downtown and then goes through the city center. Downtown Denver is a crazy place to urban skate, the traffic is wild and there are a lot of people.

What was your favorite thing you did in Denver?

The last night I was there I went to this event called Denver Roll. Once a month Denver Roll rents out a warehouse and turns it into a roller club. It is a huge space with stages, dance floors and an open bar. Everyone just gets trashed and starts falling over on their skates. I met a figure skater there that was incredible on his blades. He had been figure skating for 30 years and had only been rollerblading for a year. I also randomly met Will Enzenauer there, which was super sick. I was there until 2 am and then at 6 am drove 14 hours to Peoria, Illinois.

The serenity of a clear blue mountain lake, And the Colorado Rocky Mountain high. Photo by Kaitlin Graves.

Calb check out the Rockies

What did you go to Peoria for?

The friend I was staying with in Denver also grew up in Peoria. I rode with her to visit my family for two nights before Christmas.

Did you skate in Peoria?

When I was in Denver I bought a brand new pair of skates before going to the Denver Roll event. The next day, I was back home in Peoria and wanted to skate because it was going to snow the next day. I went out blading and my frame bolt receptor inside the boot broke. The thread snapped off of the plate and my frame broke out two miles away from my house.

Caleb’s gear.

So what did you do?

I ended up finding an old pair of Razor Cults that were in the garage that had a cuff bolt receptor in them. I had to cut the bottom-lining of my new skates and dig out the broken receptor and replace it with the receptor from the Razors to get it working again.

Did this affect the feel or performance of the skate?

Not really, but I’ve been kind of paranoid ever since that my skate are going to break again. I feel like I’m a little jinxed having brand-new $400 skates break that fast. I had only skated them for a total of four hours before they broke. It was a bit disappointing.

Where did you go after Peoria?

On Christmas night I headed to Chicago for eight days. It was a bone chillingly cold  –10 degrees Fahrenheit (-23 celcius) outside. I did not let the cold weather get to me though and immediately went skating to put on miles.

It was so cold in Chicago Caleb’s beard iced over.

Caleb Smith iced over in Chicago

What was it like skating Chicago?

I had one of the best blades of my trip there. I did a full moon skate on New Years Day covering about 10 miles and skating The Bean in an empty Millennium Park. A couple of days later I went to FNTS (Friday Nights Thursday Skate) and met up with Ben Price and Joe Dummit. I had never been under Millennium Park before so Ben took me to these underground parking garages that continued on for miles. You can skate around a garage until you get kicked out of it and then just skate to a different garage. We ended up skating underneath the city for hours.

Did you know Ben Price before your Chicago trip?

Yes. He rode his motorcycle to Des Moines once. He bought a motorcycle, rode it from Chicago all the way to Des Moines, stayed with us and rode it all the way back.

Did you go back to your favorite roller rink in Chicago?

Yes, I went back to Southside Rink in Chicago with all the derby girls. It is my favorite roller rink. They have the nicest wooden floor and always have a live DJ. Everyone there is super chill and respectful.

In front of the Wisconsin Capitol building in Madison. Photo by Sepi Shokri.

Caleb Smith in front of the Wisconsin Capitol building in Madison.

What was you’re your next stop after Chicago?

I was really fortunate and found a $1 Megabus ticket from Chicago to Madison, Wisconsin. The weather was super nice when I arrived so I immediately did a 20 mile skate around a lake to an isthmus. There was second lake on the other side of the isthmus that I wanted to skate around too, but it started snowing pretty heavily.

Did you check out the roller rink in Madison?

I was staying with a girl in Madison who quad skated. We went to a roller rink whose floor was all busted up. There were big cracks and chunks missing out of the concrete. They had put masking tape over the cracks but that didn’t help much.

I was skating backwards really fast, looking over my shoulder trying to avoid a crack and crashed into a mom. I hit her really hard back to back, I fell and swiped her legs out and she fell on her back onto the concrete floor. It was seriously one of the scariest moments of my life; I thought I had killed this lady. Everybody huddled around her and she was holding her back. I didn’t know what to do; I was like “Oh my god! Are we going to have to exchange insurance or something? But I don’t have insurance. I don’t know how that works.”

Lol, it’s not a car wreck! You can’t insure your skates in case you run into somebody!

I was really worried that I hurt this lady, but in the end she was fine. So the next day I was in a museum and decided to cut through the state capitol building to go to a coffee shop on the opposite side. As I was walking out of the building, the lady I hit was walking in. It turns out she worked for the governor at the capitol and ended up giving me a private tour of the whole capitol building.

Caleb getting a tour of the Wisconsin State Capitol. Photos by Sepi Shokri.

After Madison you headed to Minneapolis and St. Paul, was it cold and snowing there?

That is correct. It was a little snowy but it was sunny enough that the snow had melted during the day. In St. Paul I had a really nice skate around the by myself and skated to the capitol building. In Minneapolis I went skating with Mike Lufholm.

He is a great photographer; I saw you went out to get some shots with him?

That ledge roll gap I did that he took a photo of was huge and scary. I had that new city hype, wanting to represent while I was there. He shot a lot of photos of me.

Ledge roll to gap in Minneapolis photo by Mike Lufholm

Caleb Smith Ledge roll to gap photo by Mike Lufholm

What were the skating rinks like in Minneapolis?

The rink that I went to in Minneapolis was pretty rad. They actually have two different adult skates and I went to both of them. They do a Tuesday night skate and a Sunday morning skate. Many of the rinks I went to on the trip had morning adult skates on the weekends and would serve coffee. I thought that was really cool.

Were there mainly roller skaters or were there also inline skaters?

At the rink in Minneapolis most people were on roller skates but there was one other guy on big wheel blades. There were some other rollerbladers there too, but were more like figure skaters. They were super good at dance moves and tricks.

Caleb toe bonking the lamp post in Minneapolis. Photo by Mike Lufholm.

Caleb Smith with a toe tap photo by mike lufholm

Where did you head to next?

I caught a flight out of Minneapolis to Los Angeles to visit my friend Josh from Iowa that moved there. It turned out he was hosting somebody else and didn’t have room for me. I posted on Instagram that I was looking for a place to stay in LA and got a reply from Caitlin Krause. She is a rollerskater and the girlfriend of Cletus Kuhn. They offered me their couch to sleep on and I ended up staying with them for eight days. They were super friendly and it was really fun staying at their place.

Did you get to skate with Cletus Kuhn?

We went on an aggressive session with about ten other bladers. Since I didn’t have aggressive blades with me Cletus let me use his Seba skates with Oysi frames. He took me to the Seba warehouse, which was really cool. We also went on a few big wheel blade sessions and did a photo shoot under the Santa Monica Pier.

Caleb in Santa Monica. Photos by Cletus Kuhn.

Had you skated Oysi frames before that session?

No I had never skated them before. They were tall but not too tall and I could lock really well on the h-block. The length was also really good. He had his rockered so I could swivel but not loose speed or control. I really enjoyed skating the Oysi frames.

Did you do any other freeskating around LA?

I had briefly met Cletus’s friend Al Romero who told me to meet him the next day downtown to go blading. I met up with him and he became my official tour guide for Los Angeles. We ended up blading all around LA and skated through several of it’s parks. We then took a train up to North Pasadena and did a 30-mile downhill skate through neighborhood streets, trails and city parks. We ended up skating down to the LA River and stopped and had lunch at a Mexican restaurant. It was such sick skate and Al was a really cool guy to spend my day with.

LA Courthouse session with Jasen Richard, Cletus Kuhn, John Grillot and Caleb Smith. Edit by Mike Klaric.

What was the most random thing that happened to you in LA?

I did go on a really cool date in Los Angeles! I met this girl on the connecting flight from San Francisco to LA. She was from Saudi Arabia and came up to me and asked me about my coat and we started talking. We exchanged information and I found out she was also going to LA so I asked her out on a date. We walked all around Venice Beach, went to the Venice canals and had a really nice pizza dinner. We hung out at the beach for an hour or so. She is a photographer and we ended up doing a photo shoot together, which was pretty cool. She was probably one of the raddest chicks I’ve met in my whole life. She was like a little pistol.

And where is she now?

She is back in Saudi Arabia, she was just in LA visiting her sister. She did invite me out there though, so…

From the photo shoot Caleb and his date did in Venice Beach. Photos by Mashael ALObaiden

Was Los Angeles what you expected?

Yes and no. I did not expect it to be a crazy mind-blowing place. I figured it would just be like a regular city but I did not expect it to be so gross and dirty. It smelled like piss everywhere. The homeless population there was crazy. I saw homeless people in Denver and I saw homeless people in Chicago, but the homeless people in LA were insane.

Did you go on the LA Night Skate?

Kind of, there is a group that meets up on Tuesday nights. I didn’t have cell service, so I messaged them on Facebook and said I would meet them at 8:30 pm at the sculpture where they start the skate. When I got off the train I skated towards the meet up spot but couldn’t find it. I asked several cops on the street for directions but none of them knew where I was talking about. When I finally found the spot they had I already left.

I had to find a WIFI spot and contact them on Facebook again. One of these guys left a tracker for me to be able to locate them. I loaded the tracker app on my phone and started to skate to where they were but lost my WIFI connection. I kept skating around looking for WIFI spots so I could track them. For 12 miles I was just barely behind them but could never catch up to them. I skated through skid row and some really sketchy parts of downtown.

Did you ever catch up to them?

I finally caught up to them at a bar. None of them were aggressive bladers that also rode big wheels. They were just random people who had also been rollerblading for a long time. The whole night was a surreal experience

I told them about my century skate that I was trying for and they were giving me advice. They were friendly people but I just wanted to be like, “Yo I have been skating for 24 years, I don’t need your guys’ advice.” It was cool though, they bought me a beer and we just chilled and talked for a while.

Skating in Los Angeles with Al Romero

Where did you start the century skate from?

I went on one last skate around downtown LA and then caught a train to Long Beach. One of the guys I bladed with on the aggressive session with Cletus lived in the Long Beach area. He picked me up from the train station at 12:30 that night. We went to his house, hung out a bit and I went to bed at 1:30 am. My alarm went off two hours later at 3:30 am and I started my Endomondo tracker app when I left his house at 4:09 am.

I started my skate going through a massive shipping yard full of containers and towering cranes. It was still very dark outside and it was pretty scary skating through this place. Without realizing it, my map had re-routed me and I had skated 30 miles on an inland road that was parallel to the coast highway that I was supposed to be on. When I finally realized I was off course, I readjusted my map and bee-lined it back to the Pacific Coast Highway (PCH).

How far did you skate before taking a break?

After skating 50 miles I stopped at a coffee shop to rest. All I had left was $10, so I bought a coffee and a bagel. Afterwards I changed my socks and started skating again. My plan was to skate another 25 miles before taking another break. I got to 25 miles and decided that I was going to continue and do 50 miles. I wanted to see how long I could go and ended up skating non-stop until I reached San Diego.

The route Caleb skated from Long Beach to San diego.

Caleb Smith century route

Did you skate with all your stuff?

Yes. I had my backpack that weighed around 25 pounds. In my backpack I had my cloths, all my gear, a whole bunch of PB&J’s that I made, some tangerines, some trail mix, some water and coffee. It was so heavy! I was super worried about the pack and was afraid it was going to stop me. Near the end of the skate my back was hurting. I was holding my pack strap over my head and pulling it up to take the weight off my back.

What was the coastal route like?

I honestly didn’t know what to expect when I began my skate. The PCH ended up being beautiful and the weather was perfect. Most of the time I skated on a very smooth bike lane on the side of the highway.

Once you entered San Diego County you had to go through Camp Pendleton Marine Base, how was that?

To go through the base on a bike or on skates you have to register with them. You need to do it seven days in advance and I only did it two days ahead of time so I was rejected at the gate. Since they turned me away I had to change my route and skate on the shoulder of Interstate 5.

Skating along a six lane Interstate for 8 miles was really terrifying. The cars and semis were flying past me. This is the only part of the Interstate were it is legal to ride a bicycle on the shoulder. Luckily the shoulder was really smooth and easy to skate on. After 8 miles I was able to go back on the trail again. The rest of the way I skated through a state park that looked like a post-apocalyptic vast open space of nothingness.

Skating along the Pacific Coast Highway during his century skate.

Caleb Smith Century Skating down the PCH

How was skating on hills between Oceanside and San Diego?

Skating on the PCH between Oceanside and San Diego was a bit more difficult because of the hills. It was late afternoon and there was a nice breeze coming off the ocean. I was really enjoying skating through all the beautiful beach towns and people watching. However, I was starting to get physically worn down.

The sun was setting right when I was about to skate up the massive hill on Route 1 into the Torrey Pines area of San Diego. Several People warned me that there would be a big hill at the end of the skate. In my mind though I was like “whatever dude, I’ve skated up big hills”. But this hill was so freaking big and took me nearly an hour to skate up it. I had already skated 100 miles before going up this hill. Once I ascended to the summit and saw San Diego in the distance I began to celebrate my victory.

Soon after I realized my GPS quit working and I had no idea where I was going. At this point I was just trying to see how many miles I could push before my body was done. I ended up skating all the way down a trail to Sea World. By the time I got there I had logged 121.33 miles in 12 hours and 54 minutes and was officially done. I had tried to make it to 125 miles, but my ankles were too sore from the vibrations of the roads.

What did you do when you got into San Diego?

When I arrived to Sea World I called my friend Dakota Richardson, who is a blader from Des Moines that lives in San Diego. He met me at a Denny’s near where I was at and we had a huge meal. I stayed with Dakota at his parent’s house in South Park for the rest of my time in San Diego. It was a really nice area and staying with them was one of the coolest parts of the whole trip!

His dad is a renewable energy engineer and his parents grew all their own food and cooked family meals everyday. All organic, all home cooked and eaten at the dinner table. All that food was better then any meals I paid for during the entire trip. The whole time I was there we had family meals together, played board games and hung out. It was such a super sick time.

Street skating in San Diego. Edit by Dakota Richardson.

Did you do any more skating in San Diego?

The next day I big wheel bladed around Balboa Park with Dakota. Then that night I met up with the San Diego big wheel bladers and skated Balboa Park again. They were all really cool dudes to skate and hang out with. The lightening at Balboa Park was really rad, and there were still lots of pedestrians walking around there at night. I was in San Diego for four days and spent the time skating around downtown and heading to all the beach towns to skate on their boardwalks.

How did you enjoy San Diego?

San Diego was really low key. It was almost like a life reset where I was able to relax and rewind. It was the complete opposite of Los Angeles.

Caleb takes in the majestic view of the Pacific Ocean in San Diego. Photos by Dakota Richardson.

So then you flew to Austin. What was the first thing you did there?

When I arrived in Austin I skated from the airport to Andrew Broom’s apartment. He was sick but that evening he drove me to Playland Skating Rink for adult night. His car was falling apart though really bad. I skated really hard at Playland for two hours and then skated 15 miles back to his apartment. It was a pretty brutal skate because I was really worn out.

Related: Best Aggressive Inline Skates – The Ultimate Guide

How many miles have you skated so far on the trip?

I hit 400 miles of skating on my trip when I was in Austin. I ended up getting sick from Andrew while I was there, but didn’t want to become a burden on anyone. So even though I was sick, I drank a lot of beer and hung out. I don’t really drink much anymore, so it was fun and a change of pace.

One day we took a road trip to Waco to go street skating. I met Josh Glowicki and Fritz Peitzner from Dallas there. I didn’t have aggressive skates with me but it was still pretty sick to skate with those dudes.

The metaphorical finish line of Caleb’s journey. Photo by Joseph Gammill.

And did you go to the big ramp in Austin?

Oh yea, the ramp of mystery, that was the metaphorical finish line of the whole journey. I had already done everything I wanted to, I had gotten over the girl, the same girl from last time I was in Austin. So I got over her and did the century skate, I wanted my first century title, which I got. I went to a museum, coffee shop, a nice place to eat and a roller rink in every city I went to. I shed a bunch of skin and became a new me.

We went to that ramp and it was pretty huge. I went right to the top of it and rolled down it without even thinking. I went right back to the top and fakie bombed it. It was gnarly, with broken concrete, but it felt good. It felt like I wasn’t afraid of anything anymore and I could do anything I wanted in my life. Then I went home and didn’t blade at all in February which was weird because in January I bladed over 400 miles

Related: The Best Recreational Inline Skates For Beginners

Caleb with a mute grab into the Ramp of Mystery filmed by Anthony Medina


Why did you take February off?

I’ve had chronic injures that I never let heal. Caitlin is a certified occupational therapy assistant and helps people with injuries. When I was in LA she asked me when was the last time I took a break from skating and I couldn’t tell her, because I don’t take any breaks. So she told me I needed to take a break to let my body recover.

Later on in the trip when I was in Waco, Texas I was talking to Josh Glowicki and      he told me if there is something in your life that you love, then try not doing it for 30 days and see how you feel about it after those 30 days. I took this as a sign and didn’t skate the whole month of February. I kind of cheated though because February is only 28 days!

Related: The 15 Best Helmets for Inline Skating of 2023

And now you are back on the blades again?

Yes, I turned 28-years-old a couple of days ago and I wanted to skate 280-miles in March but the weather has been kind of shitty!

Caleb night skating in downtown Des Moines. Edit by Bruce James Bale.

Of all the cities you have skated in, which is the best for big wheel blading?

Des Moines! I am serious, the whole time I skated these major cities, I paid attention to the garbage, the traffic and the way the cities were designed. I started to miss Des Moines. It is big enough but small enough. It is clean and it’s nice. In fact Des Moines is so nice that I had to do one last skate before I started my month of no skating.

Related: Best Pads for Inline Skating of 2023

Did any bad things happen to you on the trip?

I did leave my camera in Minneapolis and  had to have it mailed to me, so I didn’t have my good film camera for my first six days in LA. I also was pulled over by the cops in LA for skating through an intersection too fast and ended up getting a warning ticket. It was so funny, they pulled me over and started running my ID and I was just rambling on about rollerblading because I was a little bit nervous.

I had my backpack on, was shirtless and sweaty. It was a female cop and I was just like “pull out your phone!” and I had here look at the Big Wheel Blading article about me skating in the RAGBRAI race. I had her pull it up on her phone and told her all about RAGBRAI. I think she just wanted me to stop talking so she let me go with a warning.

Caleb in downtown Minneapolis. Photo by Mike Lufhlom.

Caleb Smith in downtown Minneapolis. Photo by Mike Lufhlom.

What are your skating plans for the rest of this year?

My next distance goal is 150 miles and once I’ve achieved that; I will attempt skating 200 miles. I’m going to skate RAGBRAI again in July, but this year I’m going to do it really hardcore. I’m going to try and make a big commotion and get some momentum coming from it for myself. After the race I am flying to Anchorage, Alaska. I’m going to be there for three months to blade and work on a fishing boat to save up money.

A lady at my coffee shop has a friend who lives in Anchorage and he has his own fishing boat. He told her the fishing season starts in July, but if I come up there at the end of July I would still be able to get a job within a day by just going around and asking for one. I would like to meet up with bladers up there but I don’t know any. I’m definitely bringing my big wheel blades and my aggressive skates.

After I’m done working in Alaska I will spend a week camping at White Sands National Park outside Albuquerque, New Mexico. The family I stayed with in San Diego have a house in Costa Rica so I will be going there for a month starting November 6th. I plan on spending a month in their house and getting adjusted, before I start backpacking across South America on my blades. I want to meet and blade with different skaters around South America so please contact me.

Related: The 36 Best Inline Skates and Rollerblades

Check out the previous article with Caleb on, Caleb Smith Conquers the 467-Mile RAGBRAI Challenge.

Related Links

  1. To keep up Caleb’s adventures follow him on Facebook and Instagram.
  2. To see more skating edits check out Bruce James Bales’ Vimeo page, Mike Klaric’s Vimeo page, Dakota Richardson’s YoutTube page and Anthony Medina’s YouTube page.
  3. For more great photography visit the Instagram pages of Mike Lufholm, Joseph Gammill, Mashael ALObaiden, Dakota Richardson, Figment Art Photography and Cletus Kuhn.
  4. For information on Oysi frames visit Also follow them on Facebook and Instagram.
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  1. […] Check out more articles on Big Wheel Blading featuring Caleb Smith:– “The Land of Enchantment” Caleb Smith and Katie Baird Bladepacking New Mexico– Caleb Smith Conquers the 467-Mile RAGBRAI Challenge– Caleb Smith Goes on an Epic Winter Skate Adventure Throughout the USA […]

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