Caleb and his cycling friends at Ragbrai

I met Caleb Smith last year when he came to check out Austin, Texas. He is a fantastic, aggressive skater who has also recently gotten into riding on big wheels. I took him on his first long-distance skate, where we covered 30 miles from Austin to Manor and back. Since then, Caleb has been doing crazy amounts of skating and even participated in the 467-mile RAGBRAI challenge in Iowa. I spoke to Caleb about his experience visiting him in Des Moines a couple of weeks ago.

Caleb rolling into town.

Caleb rolling into town.

How did you find out about RAGBRAI?

I have known about RAGBRAI for a long time. It stands for the Register’s Annual Great Bicycle Ride Across Iowa, a non-competitive bicycle ride by The Des Moines Register. It’s the largest bike-touring event in the world, so living here, everyone knows about it. However, I never thought about doing it until my girlfriend decided she was going to ride in it. Jokingly, I said, “You know what? I’ll do it on blades!” and it turned into this thing I couldn’t back out of, so I just decided to do it. I went into it entirely blind and had no idea what to expect.

How many miles is it?

The route and towns it goes through change every year. The average total distance is 467 miles over seven days, with an average daily distance of 67 miles.

Did you prepare or train for this event in any way?

I was trying to do long distances in my hometown. I was getting in 15-20 miles a day. But I didn’t know what to expect, and I had no idea what the roads would be like or what the people would be like. So, the only preparedness I had was rolling around Des Moines.

Did you see any other inline skaters during the week?

I met one other skater, an older gentleman from San Diego. He was an old speed skater, and meeting him was pretty cool. It was encouraging to see that someone else was doing it, too.

Related: Best Aggressive Inline Skates – The Ultimate Guide

How many cyclists ride in RAGBRAI?

Officially, there were 10,000 riders this year. RAGBRAI holds an annual lottery, randomly selecting 8,500 riders for the week and an additional 1,500 per day. But with unofficial riders, the numbers can swell to 20,000 riders or so.

So, 20,000 cyclists and two inline skaters! How did people react to you skating?

Incredibly! It was amazing. I didn’t know what to expect; at first, I was worried that I would be alienated or shunned, but every single person gave me constant support! I had Air Force people riding by and massive teams of forty or fifty people passing me, with every single one of them cheering for me and telling me that I was crazy, they didn’t know how I was doing this, and that I was the strongest person they know. Experiencing that love was incredible; it motivated me every single step of the way.


At the start of it all.

So, how many miles did you skate on your first day?

The first day was supposed to be 55 miles, but it ended up being 62 miles.

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Oh wow, that is almost double the most you’ve done before! How did you feel after the first day doing so many miles?

The first day was exciting. I was with a group of bikers, but they were still sleeping when I woke up. So at 5:30 am, I left the first town alone and skated, knocking out 35 miles so fast. I met up with my girlfriend the next day. Immediately after pulling out of town, my wheel went into a tar crack, and I wiped it out! I scraped my knee, my shoulder, and my elbows and broke my thumbnail in half.

The fall just wrecked me, and I didn’t have a first aid kit, so I wrapped a towel around my finger and skated another thirty-something miles. It was rough, but it was also enjoyable. I didn’t want to put a bad mindset on the rest of my day, and I just wanted to keep going. At the same time, I was nervous. But all the nice views and the chance to see parts of Iowa that I usually don’t see when you’re driving in a car helped take my mind off the pain.

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Do you go to a town and camp out at the end of the day?

Yeah, there is always a meeting town every morning with parties. Then, in the ending town, there are always stages with bands playing, big cookouts, and tons of beer tents. It’s awesome because 20,000 or more people take over these little towns. It’s just RVs and tents, as far as you can see. People are camping in every person’s front yard and backyard, in parks, at gas stations, in lots with grass, and anywhere with open space. You walk around town, everybody’s drinking in public, being rowdy, and it’s just a perfect time.

So you camped the whole time? Did you carry your camping gear with you?

I started the first day with my gear, and then I was fortunate enough to meet these bikers who allowed me to put my gear in their car for the rest of the week. So that was nice of them.

How hard was it skating with your gear that first day?

It wasn’t difficult because I knew I needed to pack pretty light. I bought two t-shirts and a pair of Speedos, which were the only clothes I had. I also had a tent, a sleeping bag, and a water bottle.

Caleb getting ready for the days skate.

Caleb is getting ready for the day’s skate.

So you just skated in Speedos?

Yes, I skated in Speedos the whole time!

How did the ladies like your speedos?

The ladies liked the speedos. I was self-conscious at first because, I mean, everything was just kind of out there. But I knew it would be scorching, so I had to get past that embarrassment. I’m really glad I did because it was the last week of July, and some days I was skating 70 miles when it was upwards of 90 degrees. But yes, the ladies liked the Speedos; I got more compliments than I could count.

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How did your wheels hold up skating so many miles?

Well! I was riding a set of Rollerblade Hydrogen 125mm wheels. I’d skated them for about a month before RAGBRAI. I had to rotate them every day, sometimes twice a day, and I wore through them that week. They were done by the end of RAGBRAI, but they held up well with no cracks or chips, which was nice.

Did you make any new friends on the journey?

I made many friends and met people from all over the world, which was interesting. I grew close to the group of bikers I met. They were pretty chill, and at the end of the night, we’d hang out around a campfire, talk, tell stories, and play games. That was really nice and a bonding experience I never really got from any other rollerblading trips I’ve been on. It was also exciting because I was the only rollerblader there, and hanging out with rollerbladers is much different than hanging out with other groups of people.

You told me you met a couple traveling with a tiny house.

I met a couple on the first day on the route, and they said if I found them at their tiny house, they’d give me a beer. Arriving in these towns so full of people, there was probably no way I would ever find them. Two days later, before leaving town in the morning, I was dead; I was so tired, I just needed coffee, but I didn’t have any. I walked to the edge of the town, and at the very last yard, the couple was sitting there. They had converted a school bus into a tiny house!

Calling me over and introducing themselves again, they had made me a nice French press full of amazing coffee. They also gave me a banana, made me an egg sandwich and gave me a tour of their tiny house school bus, which was really awesome. And yea, they were just great people that I would have never met otherwise.

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Did you get a RAGBRAI jersey?

I did not. I did RAGBRAI on one hundred dollars, which I think is a pretty incredible feat because most people that do it drop five grand on the whole week.

How far was it from Des Moines? Did you hitch a ride out there?

It was about a five-hour drive on the other side of the state, on the top left corner. I didn’t know how to get there the day before and was frantically trying to find rides. I ended up meeting up with a friend heading there, too, which was convenient.

How much does it cost to participate in the event?

I did not register and did it for free. Basically, you would pay $175, and they would give you a bracelet. If you fall behind, a wagon will pick you up; if something happens to your bike, they’ll stop and help you fix it, and you get discounts on food every day. So if you pay for it, you get a lot of benefits. I didn’t have the money to register, so I was winging it there the whole time.

Do you plan on doing it again next year?

Yes, I am one hundred percent doing it this year again! I’m going to pay for it this time around though, because the benefits of being registered far outweigh the cons. I would say to anybody who’s afraid of doing things like this, you just have to try it because you’ll be surprised at what you are capable of doing. And I’m for sure going to do it again and I’m probably going to do it again for every year for the next twenty years, as long as I can.

Caleb resting on the side of the road.

Caleb is resting on the side of the road.

Do you plan on doing any other long-distance skates or marathons this year?

I do! Before RAGBRAI, I didn’t hunger for that kind of thing. But after RAGBRAI, it’s like I can’t accentuate the hunger. I want to do the North Shore Marathon, Athens to Atlanta and as much as I can fit into my schedule. Take it to a different level and just skate distances that have never been skated. I want to see if I can find parts of the Appalachian Trail that I can skate by myself, and I want to pick major cities and skate from city to city just because I enjoy it.

Awesome, I feel the same way.  I hear that one day of RAGBRAI, you can turn into a century skater.

On the 3rd, they allow you to do a century skate. It was a 70-mile day with a 30-mile optional loop. It was still before I was comfortable and knew what I was capable of. If you do the century ride, they give you a patch, and I think you get a free meal. I regret not doing it, but next year, I’ll do it for sure, and in the meantime, I’m going out to California to get my century title very soon.

So, if you pay next year, you’ll get the patch to prove it!

I don’t know if I would have gotten it this year since I didn’t pay. Maybe because I was rollerblading, they gave me one just because… I think that was the most incredible part, though. Every rollerblader wants to be famous, and that week was the most famous I’ve ever been. They coined me as a “rollerblade guy.” Everybody knew about me before I got to the towns.

When I skated into town, people would cheer, “Here’s rollerblade guy!” It was incredible; when I would pull into a town, I couldn’t count how many people were there, thousands of them in this little town. And they are just cheering for me, and man, it would fill me with so much energy, pride, and strength, and it just kept me going. It made me a little emotional because it felt crazy. It was the craziest thing I’ve ever done, and to have all these people from all parts of the world supporting me, which I didn’t know, was incredible. People gave me free food and beer and wanted to give me stuff. I was a rollerblade guy.

It’s a different kind of skating than the aggressive world we both come from, but I find it is very addictive. Plus, the risk of getting injured is much less, and it’s healthy. I also feel like it has improved my aggressive skating.

Yes, it is very healthy! I felt so strong at the end of the week. In this last year of also doing fitness and long-distance skating, my aggressive skating has improved so much. My coordination and balance have become incredible, and I’m much better at rollerblading now.

What was the worst part of RAGBRAI?

The worst part of RAGBRAI was the porta-potties! You’ve got 20,000 bikers in these small towns every night, but there aren’t close to 20,000 porta-potties. They are constantly full and stinky, and you just have to deal with it. I do not enjoy porta-potties, but this is the one time I was forced to use them.

Caleb at Babe's Marina

Caleb at Babe’s Marina

What was the highlight of RAGBRAI?

The babes! I think second to people cheering me on was when I was exhausted, and a babe would pass me on a bicycle. I don’t like to womanize, and I respect all women, but sometimes when there’s a babe in front of you with a nice butt, you can just stare at her butt for twenty miles. And biker babes have really nice butts. That was a joy; there were just a lot of beautiful women on the trip.

Obviously my girlfriend was there with her group of friends, so I never did anything I wasn’t supposed to, but it was still nice. It was nice encouragement to be a fit young guy in Speedos blading with 10,000 babes. I think the funniest part was, there was a day I skated to the halfway town, it was a 35-mile blade and I didn’t stop once. I didn’t want to, I was tired and I just wanted to get to final town.

As I skated into town, I noticed that the fire station was open, serving beer and food. They had filled up a pool, and I skated right through the station and up to the pool’s edge. I stripped down to nothing but my Speedos and jumped in. As I came up, someone handed me a beer, and then all these moms grabbed my arms and touched my body. They were asking me about my tattoos and asking about rollerblading. In any other situation, it would have been overwhelming, but at this moment, it was awesome and hilarious. I was so comfortable and just felt like I was in my prime. I enjoyed it, and my girlfriend was 20 feet away watching the whole thing happen and didn’t care.

How windy was it when you were skating?

There were a few days when the wind was really bad. They do a pretty good job mapping it to where you aren’t skating into the wind very often. However, sometimes, it felt almost impossible to skate against it. But I didn’t stop. I promised myself that on all of RAGBRAI, I would never stop because I was tired. No matter how big the hills were, how windy it was, or how tired I was.

And what was the terrain like?

It was decent. 80% of it was perfect, with nice, smooth roads. The sheriffs blocked off every road, and there was no car traffic. There were a few parts where the roads were chipped and chunky, making it difficult to skate on, but I was on 125s, so it wasn’t unbearable.

And how were the hills?

The hills were a struggle. The first five days weren’t bad, but the last two days were tough. There were probably seven noticeable hills on the last two days and four of them were the largest hills I’ve ever skated in my life. It would take me an hour and a half to skate to the top of a hill and about 15 minutes to skate down it. This was awesome because, typically, you only bomb a hill for 30 seconds or so.

Do you know how fast you’re going?

It was pretty cool because almost all the bikers had G.P.S. trackers and speedometers, and they would tell me my speed. A guy came up to me while I was skating and asked me what my average pace was. I didn’t know, so I just said 12 miles an hour. He followed me uphill and told me I was going 18 miles an hour up the entire hill. This made me feel great because I thought I was going fast. And I wanted to go fast because I didn’t want to be the slow guy on rollerblades. I wanted to show these people what I was made of.

So, after seven days of skating, how sore were you at the end of the week?

Well, by the time the race was over, I felt great. It was in the middle of the race that my body was suffering. I would get up and couldn’t really walk; I just felt stiff. It felt crazy, but then I would get some coffee and start skating. It was always challenging for the first hour and a half, but after that, man, I felt like an Olympian! You couldn’t stop me; I could keep going, and by the end of the day, my body felt like a sheet of steel.

Did you take a break from skating after RAGBRAI, or were you back on your wheels right away?

I was back on my wheels right away! I couldn’t stop it; I was addicted. The week after RAGBRAI, I probably put on another 150 miles.

At the end, it is tradition for riders to dip their front wheels into the Mississippi River.

In the end, it is tradition for riders to dip their front wheels into the Mississippi River.

Tell me about your upcoming trip.

I’m getting ready to go on an 8-city tour. I want to powerblade all these downtowns. I’m hitting Denver, Peoria, Chicago, Madison, Minneapolis, L.A., San Diego, and Austin. I want to get my century title, so I will skate from L.A. to San Diego on 142 miles of bike trails. The plan is to blast one hundred miles, camp on the beach for a few days, and then cruise to San Diego. I’m excited about it. I’ve tried once since RAGBRAI to get my century title, but it’s difficult. If you had asked me a year ago, “Are you going to skate a hundred miles in a day?” I would have said that’s the craziest thing I’ve ever heard, but now it’s not. It doesn’t seem impossible at all, and I’m really excited to do it.

Related Links
  • Follow Caleb on instagram to see where his skates take him.
  • To learn more about RAGBRAI and to register for the 2018 challenge visit
  • Contact Big Wheel Blading for any questions, suggestions, story ideas or to contribute content.
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