Caleb and his cycling friends at Ragbrai

I met Caleb Smith last year when he came to check out Austin, Texas. He is an amazing aggressive skater, who had 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 when I was visiting him in Des Moines a couple of weeks ago about his experience.

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, which is 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 at the time decided she was going to ride in it. Jokingly I said “You know what? I’ll do it on blades!” and it kind of turned into this thing I couldn’t really 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 7 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 really didn’t know what to expect and I had no idea what the roads were going to be like or what the people were going to be like. So really the only preparedness I had, was just 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.

How many cyclists ride in RAGBRAI?

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

So 20,000 cyclists and 2 inline skaters! How did people react to you skating?

Incredibly! It was amazing. I mean, 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’m crazy, they don’t know how I’m doing this and that I am 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.

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 really interesting. I was with a group of bikers but they were all still sleeping when I woke up. So at 5:30am I left the first town by myself and I skated alone knocking out 35 miles so fast. I met up in the next with my girlfriend. Immediately after pulling out of town my wheel went into a crack of tar and I wiped 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 with me, so I just 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 really 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 took helped take my mind off the pain.

At the end of the day you just go to a town and camp out?

Yeah, there is always a meeting town every morning with parties going on. Then in the ending town there’s always stages with bands playing, big cookouts and tons of beer tents. It’s awesome because these little towns get taken over by 20,000 or more people. It’s just R.V.’s and tents for as far as you can see. In every person’s front yard, back yard, in parks, at gas stations, lots with grass and basically anywhere with open space there are people camping. You just walk around town, everybody’s drinking in public, being kind of rowdy and it’s just a really good 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 that allowed me to put my gear in their car for the rest of the week. So that was really 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 brought two t-shirts and a pair of Speedos, so that was the only clothes I had with me. I also had a tent, a sleeping bag and a water bottle.

Caleb getting ready for the days skate.

Caleb getting ready for the days skate.

So you just skated in Speedos?

Yes I skated in Speedos the whole time!

How did the ladies like your speedos?

The ladies really liked the speedos. I was really self-conscious at first, because I mean, everything was just kind of out there. But I knew it would be really hot so I had to get past the embarrassment of that. 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 definitely liked the Speedos, I got more compliments then I could count.

How did your wheels hold up skating so many miles?

Really 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 really well with no cracks or chips, which was nice.

Did you make any new friends on the journey?

I made a lot of friends and met people from all over the world, which was really interesting. I grew really close to that 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 was a bonding experience that I never really gotten from any other rollerblading trips I’ve been on. It was also really interesting because I was the only rollerblader there and hanging out with rollerbladers is much different then 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 find them at their tiny house then they’d give me a beer. Arriving in these towns so full of people there was probably no way I was ever going to find them. Two days later, before leaving town in the morning, I was totally dead, I was so tired, I just needed coffee but I didn’t have any coffee. I walked to the edge of the town and at the very last yard the couple was sitting there. They had 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.

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 all the way on the other side of the state, on the top left corner. The day before I didn’t know how I was going to get there and was frantically trying to find rides. I ended up meeting up with a friend who was heading there too, which was really convenient.

How much does it cost to participate in the event?

I did not register and did it for free. But basically you would pay $175 and they 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 there is a lot of benefits that you get. I didn’t have the money to register, so I was just winging it there 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 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 really have a 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 in my schedule. To take it to a different level and just go skate distances that have never been skated. I want to see if I can find parts of the Appalachian Trail that I can just skate by myself and I want to pick major cities and skate from city to city, just because I really enjoy it.

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

On the 3rd they give you the option of doing 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 actually going out to California to try to get my century title very soon.

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

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

As soon as I would skate into town people would be cheering, “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 and 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, that I didn’t know from all parts of the world supporting me was incredible. People gave free food and beer and just wanted to give me stuff. I was rollerblade guy.

It’s definitely a different kind of skating then 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 so much better at just 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 single 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 where 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, 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 and they were serving beer and food. They had filled up a pool and I just skated right through the station and up to the edge of the pool. 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 touching my body. They were asking me about my tattoos and asking about rollerblading. In any other situation it would have been overwhelming but in this moment it was awesome and it was hilarious. I was so comfortable and just felt like I was in my prime. I really 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 where the wind was really bad. They do a pretty good job of mapping it to where you aren’t skating into the wind very often. However there were times where it felt almost impossible to skate against it. But I didn’t stop. I made a promise to myself, that on all of RAGBRAI, to 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. I’d say 80% of it was perfect with nice, smooth roads. The sheriffs blocked off every road and there was absolutely no car traffic. There were a few parts where the roads were chipped and chunky which made 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 really 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. I had a guy come up to me while I was skating and asked me what my average pace was. I didn’t really know so I just said 12 miles an hour. He had been following 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 really 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 time the race was over I actually felt great. It was in the middle of the race that my body was suffering. I would get up and I couldn’t really walk, I just felt stiff. It felt crazy but then I would get some coffee in me start skating. It was always really difficult for the first hour and a half, but after that, man I felt like an Olympian! You couldn’t stop me, I could just keep going and by the end of the day my body felt like a sheet of steel.

Did you take a break 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.

At 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 just 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’m going to skate from L.A. to San Diego on 142 miles of bike trails. The plan is to blast one hundred miles and camp on the beach for a few days and then cruise to San Diego. I’m really 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.

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