Confessions of a Middle Aged Man in Lycra – RAGBRAI

by | Aug 21, 2025 | Sports, Travel | 78 comments

The Register’s Annual Great Bicycle Ride Across Iowa (RAGBRAI) is Iowa’s Burning Man, a 7 day bike ride across the state with 30,000 of your closest friends. The stars aligned for me to participate in this year’s edition.  My brother has an RV, he lives near the starting town, and he was going to drive support for a buddy of his and he had another spot open.  So I signed up, bought my plane tickets, shipped my bike and headed for Iowa.

Day 0

No riding today.  There was an expo in the start town of Orange City, so named for the citrus groves that surround the city.  Or maybe it’s because of the area’s Dutch heritage.  We wandered around the expo, collected some SWAG, picked up our bikes, and headed back to my brother’s house to get ready for the ride.

Going Dutch

Day 1

Route: Orange City to Milford

Distance: 79 miles

Elevation Gain: 1815 feet

Fatalities: 0

We started riding just after dawn.  Young ladies in traditional Dutch outfits waved to us as we rolled out of town.  Riders slowed to a crawl in one of the very first turns of the day, as people were administering first aid to a fallen rider.  Fortunately he survived thanks to CPR from one of the riders and a defibrillator that a nearby patrolman had in his car.

As would become a habit for the week, we stopped for pancakes in the first town, ate ice cream at a roadside stop, and peed in the corn fields because the lines at the lavishly decorated outhouses were too long. 

Choose your crapper.

Our lodging for the night was at a gas station on the side of the road just out of town.  It was actually nicer than it sounds.  They had a live band playing well into the night, but since we were well down the parking lot, we were able to get some sleep.

Day 2

Route: Milford to Estherville

Distance: 41 miles

Elevation Gain: 1115 feet

Fatalities: 1

Day 2 was a pretty short ride that took us up into Minnesota.  Rumor has it that the trees in Iowa lean north because Minnesota sucks or maybe the other way around, but I saw no evidence of it.  The week’s first fatality happened in the first corner in Minnesota.  The 62 year old rider collapsed and was declared dead on arrival at the hospital.  It’s not clear how this could have happened as it was a short day, not strenuous and the weather was cool.  My only guess is that Somali pirates out on the lakes got to him or Walz’s wife frightened him.

Welcome to Minnesota!

Once back in Iowa the route passed a winery which I scoffed at as my wife works at a winery and brings home plenty of good free wine, but now I regret not stopping just to try it out.  Shortly after the winery we passed through Superior, an ambitious name for a town of about 150 people.  The day ended in Estherville where we passed some beautiful homes on the way into town.  Estherville must have been thriving at some point, but since the 1970s it has lost about 25% of its population, and the downtown has a lot of empty storefronts, many of which suffer from 1970s architecture.  

We got sandwiches at a food truck that billed its food as “One of the Best Pork Tenderloin Sandwiches”.  Not “the best”, but pretty good.  Definitely up there.  Gotta love that Midwestern modesty.

Our overnight spot was on a farm on the edge of town.  The scenery reminded me of the English countryside in Clarkson’s Farm, but maybe any place with green rolling hills would make this California boy think that.

Safely back in Iowa.

Day 3

Route: Estherville to Forest City.

Distance: 75 miles

Elevation Gain: 1330 feet

Fatalities: 1

The second fatality happened on the way out of town in the morning.  Maybe people need to do a little training before doing this ride.  It’s interesting that these incidents all happened in the morning and at intersections.  The rumble strips at intersections seem to cause a panic in the riders, and the pack is more bunched up in the morning, so maybe something about that combination really raises the stress level for some people.

Early in the ride my legs started feeling crampy.  This was not good as there were miles to go before we slept.  I noticed that my seatpost must have slipped, so I pulled over to the side of the road to fix the problem.  Almost immediately riders from the Air Force and Space Force swooped in to see if I needed help.  They had about 150 riders providing mechanical assistance to anyone who needed it, which was pretty cool.  Anyway, I fixed my seatpost, which resolved the cramping.

If they really want a challenge, they should bounce a basketball the whole way.

Near Titonka I passed some guys on unicycles and a guy riding his BMX bike backwards.  I guess the ride isn’t enough of a challenge as it is.  As the day wore on the temperature got hotter and the winds kicked up.  People were getting tired and grew quiet.  There was an option to do a loop that would make it a 100 mile day, but I opted out as it wouldn’t reveal much new scenery, and I knew the next day would be even more difficult.  I also was riding the optional gravel sections which I figured was enough added challenge.  

At Crystal Lake, home of the world’s largest bullhead, people were jumping in the water to cool off.  It looked tempting, but I wanted to get to the finish and have a beer.  The route into town turned north, which I looked forward to, as it would give us a nice tailwind, but as soon as we made the turn it felt like an oven, as we were moving the same speed as the wind and therefore didn’t get any cooling from the wind.  Fortunately some of the local residents were spraying their garden hoses on the riders.

Something tells me they are exaggerating.

Forest City is the home of Winnebago, and our campground was at the edge town at the Winnebago Rally Grounds.  To get there we rode our bikes to the levee but the levee was dry.  In the evening we watched a spectacular lightning show to the southeast over Mason City where Buddy Holly crashed.

Day 4 

Route: Forest City to Iowa Falls

Distance: 73 miles

Elevation Gain: 1554 feet

Fatalities: 0

Starting early to be the heat. I said heat.

This was the hardest day.  Almost all due south into a hot, raging southerly wind.  There was a guy on a penny farthing who really had nowhere to hide.  I could at least draft behind other riders, but he had no such option.  The guys on unicycles really appeared to be suffering.  The guy I had been riding with had to bail out about 20 miles before the finish as he was suffering in the heat.  The last leg into Iowa Falls paralleled the river, and people were swimming to cool off, but I wanted to get to the finish and air conditioning as the temperature was hovering around 100 degrees. 

Must be fun in the wind.

Shortly before reaching Iowa Falls my brother texted me the location of our overnight spot, which was a farm about 12 miles northeast of town.  I was a little annoyed at the extra distance, but I didn’t want to complain lest I become responsible for finding campsites.  With the help of Google Maps I plotted a route to our overnight spot.  In general navigation in Iowa is not a big problem as the roads are in a grid.  The choice was between the highway and gravel roads of unknown condition.  When I got to the highway I saw all the speeding trucks and narrow shoulder and chose the gravel roads.  Some of the gravel roads were better than paved California roads, but other roads were freshly graveled, which made the pedaling slow going.  Eventually I made it to the farm where I cooled off in the shower.  Our hosts that night cooked dinner for us and the other cyclists who were staying on the farm.  Great hospitality was one of the best features of the ride. 

Day 5

Route: Iowa Falls to Cedar Falls

Distance: 57 miles

Elevation Gain: 1148 feet

During the night a huge storm dropped about 2-3 inches of rain.  I sure was glad to be in an RV rather than in a tent.  The gravel road from the farm to the paved road became a little sloppy due to the rain.  I enjoy riding in the slop, but the other guy had narrow tires and had to take it slow, so I waited up for him as I was the navigator.  Back on the course I left the other guy to his own devices as there were a lot of optional gravel sections to be enjoyed.  They started out slick due to the rain, but they dried out as the day progressed and became hero gravel, smooth and fast, much like me.  

Rolling into New Hartford people started bunching up on a downhill at high speed like in a peloton.  While rubbin’ is racin’, RAGBRAI isn’t supposed to be a race, and the skills and sobriety of the other riders were unknown.  Fortunately we made it through without incident and without becoming a statistic.

Their milkshakes bring all the riders to the yard.

In town I stopped at the New Hartford Creamery for a chocolate shake, which I highly recommend if you are in the area.  Walking out of town I spotted a bike with massive wheels.  Not a penny farthing, but more like a quarter quarter.  Then I noticed the guy holding the bike was massive.  Then I noticed it was David Robinson.  Too bad he hadn’t been riding the day before so he could block the headwind, and I could say that I was drafted just behind The Admiral.

You know what they say about a guy with big wheels?

The ride finished in Cedar Falls which has a nice downtown.  At an old diner we got a Made Rite, which I guess is a version of Loose Meat, which is something that needs a new name.  It contains Iowa’s basic food group, brown.  It must be an acquired taste.

Our overnight spot was at another farm about 10 miles out of town.  As the sun went down the fireflies put on quite a show over the soybean fields, which was fascinating to those of us from places without fireflies.

Day 6 

Route: Cedar Falls to Oelwein

Distance: 40 miles

Elevation Gain: 1287 feet

The shortest way back to the route was by the highway, which nobody wanted to ride.  The others who stayed at the farm got a ride down to the route, but I decided to backtrack to the west on a gravel road and head south on another gravel road to the route, the grid making it impossible to get lost.  

One of the gravel segments took us through Amish country complete with horses and buggies and large amounts of laundry drying on the lines.  I saw an Amish kid selling cookies at the side of the road.  His hair was perfect. 

Ah-ooo, the Amish of Iowa.

The day finished in Oelwein, which was the subject of the book Methland.  I didn’t see any meth, but the beer was flowing, as this was the shortest day and people had time on their hands.  We stayed at an RV park on the edge of town.  The owner must have been a descendent of the original German settlers, as our names had to be on a list to get in, we were given wristbands, and there were rules and regulations posted all over.  There was even a barbed wire fence around the camp.  I’m not Jewish, but I do share a last name with many of (((them))), so maybe I should have been nervous.  The lack of visible guard towers reassured me.

Day 7

Route: Oelwein to Guttenberg (not Gutenberg)

Distance: 67 miles

Elevation Gain: 2604 feet

The roads transitioned out of the grid and into the Driftless Region, which is a region that the glaciers missed in the last ice age.  The area is marked by hills and valleys and winding roads.  Midway through the ride rain started to fall as did my mood.  My internal voice started wandering.  “Riding in the rain sucks.  The rain is going to wash away my Chamois Butt’r and I’ll get a saddle sore.  Maybe I should catch the SAG Wagon to the finish.  Shut up.  This is part of the experience.  It’s a warm rain and it will pass.  Don’t be such a wuss.”  Hopefully the voices in my head didn’t bother anyone.

Indeed the rain did clear by the time we hit the hills.  All week people had been concerned about the hills on the last day.  They were 300 feet!  They were 2 miles long!  I can understand the worries of the less experienced, but hearing this from people on expensive carbon bikes wearing tight clothing made me internally roll my eyes.  I have longer climbs out my front door.  But who knows?  Maybe after a week of riding they will be harder than they sound.  

What did have me worried were today’s gravel segments which the organizers said were more technical and rough than the others, so I was expecting chunky gravel or even baby heads.  Luckily the roads were nice and smooth, just some steep downhills that I feared would be slick due to the rain.  I took it easy as the roads dropped us into some beautiful valleys.  

The Fast and the Furious, Iowa Driftless.

Back on the pavement there was one last steep descent to the Mississippi in the town of Guttenberg (note the extra t), and just like that the ride was over.  We waited in line to do the traditional tire dip in the river and have our pictures taken.  Time for one last ice cream before dropping off our bikes at the logistics company to ship them home.  I was ready to keep riding, but the real world was calling.

End of the road.

Tips if you plan to do it yourself

  • Bring cash.  The cellular network and internet in many of these small towns get overwhelmed so credit card processing is unreliable.
  • Get an RV.  Better yet, get a friend or a family member who has an RV.
  • Bring bug spray.  The mosquitos or something ate me alive at the campsites.
  • Stay on top of chamois butter, hydration and electrolytes.  You don’t want saddle sores, dehydration or cramps.
  • Bring wipes.  You might not need them, but it’s comforting to know you have them in case of an emergency, IYKWIM.
  • Be prepared mentally and physically to ride some extra miles to the place you are staying.
  • Leg warmers not required.

About The Author

JaimeRoberto (carnitas/spicy salsa)

JaimeRoberto (carnitas/spicy salsa)

Am I being detained?

78 Comments

  1. Furthest Blue pistoffnick (370HSSV)

    much new [Iowa] scenery

    Near the Mississippi can be pretty. Otherwise, Iowa is not often associated with scenery.

    https://www.youtube.com/watch?v=-mn16d8hs04

    • Furthest Blue pistoffnick (370HSSV)

      blockquote fail. Bad coder – no Mountain Dew!

      I lived upriver from Guttenburg in Dubuque.

      Beautiful, huge Victorian style house. We counted over 700 trick-or-treaters our first year. After the third trip to the store for more candy, we gave up and shut the lights off.

      • Ted S.

        Blame it on AI.

  2. Sean

    Tips if you plan to do it yourself

    Yeah. No worries here.

  3. kinnath

    RAGBRAI was one of the hottest, steamiest weeks we’ve had this summer.

    I hope you enjoyed your time trapped in fly-over country.

    • Ted S.

      RAGBRAI was one of the hottest, steamiest weeks we’ve had this summer.

      Enough with the euphemisms. :-p

      • JaimeRoberto (carnitas/spicy salsa)

        Lots of time in the saddle.

  4. The Late P Brooks

    Very nice. Glad you enjoyed it.

      • UnCivilServant

        I thought it was illegal to race non-german cars on that track.

      • Sensei

        I think they need to be road legal for the non-sanctioned racing. I believe this is UK legal.

        In the beginning of the video he removes a wing because he wasn’t sure it was going to meet German legality requirements. He also mentioned it was going to slow it on the straights.

  5. Furthest Blue pistoffnick (370HSSV)

    The Amish generally don’t like their picture taken.

    • JaimeRoberto (carnitas/spicy salsa)

      It seems to depend on the specific group of Amish. Some are stricter than others. I asked the kid before I took his picture.

      • Toxteth O'Grady

        I like his confident pose. His haircut makes him look like DJ Conner.

    • UnCivilServant

      I don’t blame them, I hate getting my picture taken.

      • Akira

        When I see children getting addicted to screens before they can even talk and everyone ruining their health with garbage food, I get tempted to join the Amish sometimes.

    • Rat on a train

      Must be one of those progressive Amish. He also has exposed buttons.

    • Evan from Evansville

      Oooh. I forgot about that.

  6. Beau Knott

    As a former Iowan I lol’d at the description of Iowa’s basic food group 😃
    As always, great pictures and great descriptions. Kudos!

  7. Not Adahn

    Walking out of town I spotted a bike with massive wheels. Not a penny farthing, but more like a quarter quarter. Then I noticed the guy holding the bike was massive. Then I noticed it was David Robinson.

    That’s not something you get to write every day.

  8. The Other Kevin

    You have my admiration. I cannot stand anything endurance. I’m building up to 45 minute cardio sessions at the gym and I hate it. I suppose seeing the sights as you go would be helpful, though.

    • Nephilium

      For me, I need a destination to bike to. Biking across town to meet a friend for lunch, that’s fun! Biking in a circle for hours… hell no. Stationary trainer for hours… fuck no.

  9. Akira

    There was even a barbed wire fence around the camp. I’m not Jewish, but I do share a last name with many of (((them))), so maybe I should have been nervous. The lack of visible guard towers reassured me.

    On the “Great Miami River Recreational Trail” just a little north of Dayton OH, there’s a section that goes through an industrial district. I guess the properties on both sides felt the need to put up a chain link fence with barbed wire, so you’re riding between those for a mile or so. Like the goddamn Tour de Auschwitz.

    That was one reason among many that I decided that the immediate Dayton area is not scenic enough to justify me riding all the way down there from where I am.

    • Gender Traitor

      What?? You don’t want to get mugged and have your bike, phone, etc. stolen along the river in view of the lovely Dayton Art Institute, Masonic Temple, and downtown skyline? Where’s your sense of adventure? 🙄

      • UnCivilServant

        I prefer my adventure in fictional form.

      • Akira

        Haha no shit. I knew I had entered Dayton when I saw spraypaint on every conceivable surface and the litter-to-grass ratio tipped the other way.

  10. Not Adahn

    We got sandwiches at a food truck that billed its food as “One of the Best Pork Tenderloin Sandwiches”. Not “the best”, but pretty good. Definitely up there. Gotta love that Midwestern modesty.

    There was a trailer near where I worked in Austin that had excellent tenderloin sandwiches, even better fries and the fourth-best burgers in the city. Their “Austinite” (pepper jack, bacon, guac) was just wonderful. Then the restaurants lobbied the city and got food trucks banned.

  11. Not Adahn

    Woot!

    Finished the paperwork for the Range Master program, it weighed in at 100 pages. Now to keep reading the rulebook for the next two months and see if I can build up a big enough base of support to get through the review in October, where I may also RM a chunk of Race Gun Nationals.

    • Evan from Evansville

      “…it weighed in at 100 pages.”

      Oooh, that’s a new, exciting comparison game for journos to learn! “Steve Lardman’s obesity directly contributed to his death, weighing in at 753 pounds at the time of his death. That’s the equivalent of 239,466,824,717,538,828,191 pages of A4.”

      • Evan from Evansville

        *slaps face* I’m distracted with a good Cubs game. I would not have reused “death” were I focused.

        Oooh, that’s a new, exciting comparison game for journos to learn! “Steve Lardman’s obesity directly contributed to his death, weighing 753 pounds when he died. That’s the equivalent of 239,466,824,717,538,828,191 pages of A4.”

  12. The Late P Brooks

    OT – 260HP and 1,000 kilos of fun for some reasonable money, but a ton of time and fab work.

    I haven’t been following that.

    I have, despite my aversion to “podcasts” been watching Chris Harris and Friends, or whatever they call it. Harris and three other guys talking about cars, mostly. I don’t really know who his friends are. It doesn’t matter. The important part is they’re not blathering self-obsessed twats. They are smart and knowledgeable and occasionally hilarious.

    • Sensei

      That particular channel is guy who has race shop at the Ring, but races all kinds of cars there for grins.

      He plowed a Tesla Model S Plaid around there. It was textbook example of all go and no stop. I believe he also managed to heat soak it enough that it pulled power, but I can’t remember if that was Model 3 or the Model S. It still did well because of the power, but it didn’t look fun.

      Nürburgring Hot Lap | Corvette ZR1X | Chevrolet

      I wasn’t totally paying attention, but I think he “only” got 198 or 199 MPH. I was waiting for the magic 200 MPH. The thing is a POS.

  13. The Late P Brooks

    I thought it was illegal to race non-german cars on that track.

    It’s technically a public toll road.

  14. Bobarian LMD

    Every day involved a gain in elevation? Maybe you should try going the other way?

    • UnCivilServant

      It’s the old school road – both ways are uphill.

    • robc

      I can’t figure out how the Mississippi was uphill. It should have been all downhill to the river.

      • UnCivilServant

        You assume a perfectly perpendicular course, or one facing downstream. If you have a more acute course facing more upstream than down, you can gain elevation while approaching the river.

  15. DEG

    The Register’s Annual Great Bicycle Ride Across Iowa (RAGBRAI)

    Why did I read that as RAGBRA?

    • JaimeRoberto (carnitas/spicy salsa)

      Because you have a dirty mind?

    • Evan from Evansville

      I read its meaning as “BBQ rag.”

  16. The Late P Brooks

    That particular channel is guy who has race shop at the Ring, but races all kinds of cars there for grins.

    Misha something or other. I watch his stuff occasionally. He did one with Ben Collins (the OG Stig) in which he was co-driver/navigator/coach giving Collins pace notes. It was pretty interesting.

  17. DEG

    Some of the gravel roads were better than paved California roads

    Better than paved California roads is a low bar.

  18. Threedoor

    “Almost immediately riders from the Air Force and Space Force swooped in to see if I needed help.”

    Chairforce, even sitting down exercising.

    Amish kid selling cookies. I bought an Amish scooter bike this summer. It’s cool and weird, has zero ground clearance and is terrifying to ride.

  19. Not Adahn

    Were the residents of Orange also selling Dutch wives and Dutch babies?

  20. Threedoor

    I have no idea who David Robinson is but I need to know More about his bike.

      • Threedoor

        I figured he was some sort of sports guy.

        Good for him that he saved his money and bought into the franchise. Smart.

      • slumbrew

        Annapolis grad (thus, ‘The Admiral’), accomplished pianist, pro ball player. He’s always been an impressive guy.

        Saw a feature on him & his son before the last Olympics – seems like a total mensch.

      • Fourscore

        I was always curious about how DR got into the Naval Academy, naval career, etc. Now I know.

      • Threedoor

        Guy I went to high school with got a slot at the naval academy. They told him he was too tall and DQd him.

        He must not have been tall enough at 6’7”

      • UnCivilServant

        Was he trying out for the Submarine Corp?

      • Threedoor

        Uncivil, I’m not sure what he was after in the navy. I’m not sure officers get to choose.

        I was army enlisted we had a ‘choice’ upon joining also known as “needs of the army” after you sign the dotted line.

      • UnCivilServant

        I was trying to come up with a portion of the Navy where “too tall” might be reasonable as a detriment.

        Or do we design our warships for short kings?

      • robc

        IIRC, Robinson was under the height requirement when he started, but grew like 5 inches his freshman year.

      • Nephilium

        One guy in our group joined the Navy and wound up serving on a submarine. He was ~6 feet tall, and complained that he could barely stand up.

      • slumbrew

        https://vault.si.com/vault/1985/01/28/as-he-grows-so-grows-navy

        “The height limit for midshipmen entering the U.S. Naval Academy is 6’6″, but 5% of an incoming class can be as tall as 6’8″. Robinson entered the Academy in the summer of 1983 at that height and sprouted three more inches in a year. ”

        Ooof, that had to be uncomfortable. He grew 2 more inches after that, too.

      • Threedoor

        Completely explains all the short marines.

      • slumbrew

        You’re options must be limited when you’re over 7′.

      • slumbrew

        “You’re”?!

        WTF.

      • Threedoor

        That’s pretty sweet.

        I’m 6’5”.
        Usually around 250 lb, finding a bike that’s big enough is relatively easy. One that I don’t break components just being me is harder. Toss a back pack and clothes on me and I’m 300 pounds.

      • Not Adahn

        Pedals: Not provided.

        A $5k bicycle that you have to provide your own pedals? Da-absolute-fuq?

      • Sensei

        Think of it like buying an expensive rifle with no optics. You pick what you want.

    • Threedoor

      Maybe he was 6’8”.
      Really broke his spirits. No idea what became of him after graduation.

  21. Plinker762

    Was there a camp at Crystal Lake?

  22. Fourscore

    Nice travelogue, JR. I was familiar with some of the places you got to see.

    Iowa and Southern MN are pretty much interchangeable. Nice folks, quiet towns.

  23. Evan from Evansville

    “Young ladies in traditional Dutch outfits waved to us as we rolled out of town.”

    Flag on the Field: You suffer a 10-wank penalty for not documenting these lovely young ladies, traditionally attired, for my viewing pleasure.

    Your other pics are fantastic. (So why wouldn’t the one with the Fräulein?! *stare intensifies*) That Amish little’un and his little’un pony? *mwah* Good eye. (Iowa looks a lot like Indiana. This should be of no surprise, but I’m kinda shocked it’s more non-flat than I expected.)

    • kinnath

      Iowa is not flat. It is rolling plains with bluffs along the river. Driving south through Illinois is some of the flattest ground that I have ever seen.

      • UnCivilServant

        The flattest ground I have ever seen was in Texas.

      • kinnath

        It does get pretty flat along the IA/MN border though.

    • Evan from Evansville

      Iowa’s one of (maybe?) 14 states I haven’t been to. I have been to Alaska and Hawaii, tho. Only thing Iowa has for me? The Cubs’ AAA team is there. Their AA team is in South Bend and I’ve been a few times.

      I’m sure Nebraska’s the flattest land I’ve been to. *shrug* Could be cuz I grew up here, but I love Indiana and Midwest scenery. Pleasant, with rivers, farmland and forests, four seasons, and free from major extremities.

      (Except tornadoes.) To be fair, Evansville is in the tippy tippy tiptoe end of Tornado Alley. I remember the ones from my youth, only a few ‘serious’ by our house. Funnily enough, one was on June 8, 1995, my bro’s 14th birthday. One in 2006 was maybe a mile away and killed ~36 in a trailer park.

  24. Evan from Evansville

    When I first saw the Fatality entry, I chuckled and assumed it’d become a running gag of some sort. Damn.