“Oh, but now old friends are acting strange
And they shake their heads, and they tell me that I’ve changed
Well, something’s lost, but something’s gained
In living every day
I’ve looked at life from both sides now
From win and lose and still somehow
It’s life’s illusions I recall
I really don’t know life at all“

~ Joni Mitchell

Every year it takes longer and longer for me to write the wrap up post after the ride. At some point I finally commit to writing it. Then it’s just me and a laptop, early in the morning, henpecking in my awkward typing style until I have it done. No AI, no edits, I typically write it and publish it. Then I usually go back a week later and fix the errors. This year I wanted to capture the ride while it was still fresh in my mind, so I forced myself to get it done now.

I spent some time updating and cleaning up the website in early July, and it was really fun to look back on all of the posts over the years. I had forgotten some of the “one and done” participants, and some of the adventures. I tend to live in the moment during the rides, which is why they are so cathartic. I encourage everyone to take pictures, and when I sit down to write, that’s where I start. I review all of the photos, pick the ones with the greatest emotional connections and write the recap.

Going into this year’s ride, I have a lot of “stuff” rattling around in my skull. So much has transpired since last year’s ride that it’s hard to grasp. Overall, I consider myself very blessed. Not in a religious sense, as I’ve never been comfortable with religion, but in a spiritual sense. After last year’s ride I drove to Nebraska with friends and repeated my 2024 Gravel Worlds singlespeed win. As someone who lives with imposter syndrome, repeating a win and putting 30 minutes between me and second place made it very real for me. In all my years of racing, and all the races I’ve been in, I have now crossed the finish line in 1st place a total of twice.

In February, Cheryl and I flew to Turkey and Thailand for an amazing 2 week adventure to celebrate our 30th year of marriage. I was probably the strongest (physically) that I have ever been this past winter. My job is amazing – coming up on 4 years there, and it just feels like where I belong. We just bought a new house, after 25 years in the old one, and it’s perfect for us.

All of that juju in my corner is not something I’m accustomed to. My life has always been a series of ups and downs, with downs generally leading the race, leading me to believe that I was not worthy of all of the goodness that the world has to offer. But the game-changer for me has suddenly been the fact that I don’t have to live in the valleys anymore. During this same past year, I was diagnosed with severe spondylosis – I have no disc left between my bottom two vertebrae. It’s bone on bone and I have constant pain and discomfort. Oh, and I have cancer.

Despite those 2 diagnoses, I have somehow managed to just mentally surf the wavetops. Both are out of my control, and manageable, and so I don’t dwell on them. Some days I feel like I can barely get out of bed, and others I feel invincible. I just take the good with the bad.

Now, in the final days prior this year’s Windy, I have ridden 641 miles for the entire year. 141 more than we cover in only 4 days. That’s thousands less than any year in past 20(?). After Gravel Worlds last year, I told myself that I would only ride for fun in 2026. No races, no training, no riding because I have to, only riding when I want to. It has been a welcome relief, allowing me to focus on other things. But I am not physically prepared for this trek through the endless hills of the Driftless area. I am, however, mentally ready because I know I can do anything I set my mind to. And, as expected, this ride is not a physical event for me, it’s a mental one. With all that as the backdrop, I made the most of it this year.

Fast forward to today – August 8th, 2026. The Windy is over. We all made it home in one piece, though there were far fewer “Full Monty” riders this year than in almost all of the previous iterations. We had some join us on Saturday, and some who had to tap out on Sunday. Regardless – the ride rolled, as it always does, and there was a beginning, a middle, and an end. And I made it through with absolutely no issues. In fact, I got stronger every day, and could have ridden much faster and farther. But that’s not what this ride is about.

Day 1 launched from our new house in Menomonee Falls. I no longer have the luxury of a long circle driveway that can park an endless number of cars for 4 days. I appealed to the local church about “borrowing” a few of their parking spots for 4 days, but they declined to respond. So, with some creative drop-offs, ride-tos, and carpooling, everyone made it to the start line on time.

In year 1 we had 4 riders. Year 2 was 7. Once I realized this was going to be an actual thing, I had visions of grandeur. I imagined a rolling city-full of people, not unlike RAGBRAI. At it’s peak, we had almost 30 riders, plus some day 1 stragglers that joined us for breakfast and then rolled back home. It was terrible. Disorganized and chaotic, we never really gelled. The ideal size for this ride is 10-12 riders and a SAG dude. This year, we had 9 total riders, although only 6 at the start line. A dozen guys is the perfect amount for sharing the work on the road, sharing the overall costs, eating at a tiny restaurant in the middle of nowhere, and accommodating at a VRBO. Bigger than that, and it becomes a rolling circus.

bc and Finn scoped out a new breakfast spot in an old familiar building. Our longtime Day 1 breakfast spot (Alma’s) closed last year and this year it reopened as “The Early Bird”. Our waitress struggled a bit with our orders, but she was a good sport. The breakfast was spectacular, and we rolled out fat and happy.

From there we rolled through the rural middle of nowhere communities of Farmville, Smalltownville and BassAckwardville, all under cover of a growing cluster of storm clouds. At exactly halfway to our destination, the clouds could hold no more and it started to rain. We’ve had rain on almost every Windy. Some has been negligible and some has required us to take cover. But it usually waits until at least Day 2 to hit us. This storm lasted over 24 hours, through the night and well into Day 2. Not ideal, but we have to take the good with the bad. Before the rains came, these kids did their best “Blake in Crocs” and rode with us for a 1/2 mile without hitting a single mailbox.

Once the rain hit, we rode in wet conditions for the next few hours. A too-long stop at Wedl’s for some smash burgers should have been a reward, but I was soaked to the bone and got so chilled that my teeth were chattering uncontrollably by the time we left. It took a good 10 miles or so, and a vest and windbreaker, to get somewhere close to warm again.

We rolled into base camp in good shape and Kevin got right to washing all of the bikes. And we immediately tossed our filthy kits into 2 washing machines.

I was definitely blindly optimistic when I chose a pair of crisp, white socks Friday morning…

The evolution of switching from 2-up hotel rooms in 3 different cities, to 2-up rooms in a base camp city, and finally VRBOs in a base camp city has produced the best (non-riding) parts of the adventures. We all eat together, like a family, and we all hang out in one house. First of all, a house that can sleep 14+ is always a unique house. That alone creates conversations. But secondly, just like a family, the house allows everyone to follow familiar routines, while also being a part of the overall ecosystem. Some guys go to bed early, some get up late, we all eat together, we all hang out together. That proximity naturally puts everyone at ease and creates a sense of tribe that hotels never could.

Day 2

On Saturday, August 1, I turned 57 years old. I’ve never been a big fan of celebrations of me. They make me feel uncomfortable. But I did have a lot of time to reflect that morning. I woke up at 5:55, got up, made some coffee and sat alone for a little while. It was pouring rain, and about 63°. Fine for a short ride, but not 125 miles. It looked like a day of misery was on tap for all of us. So instead, we waited. And waited. And waited. Ultimately leaving at 1:30 and covering only 70 miles – mostly in the rain. So, seven and a half hours of sitting around. Thinking. And in that time I realized a few things:

1. I was designed to ride 100 miles on a bicycle. Some people are born to teach, or invent things or become the President of a country. I was born to ride a bicycle 100 +/- miles. Trained or untrained, I can do it with my eyes closed. Unfortunately, 57 is way too late to discover that talent, but such is life.
2. I’m 57. I looked around at the guys I was riding with – some younger, some older – and I realized that the clock is really ticking now. On the bike, I feel half my age. I ride with people half my age and I compete against people half my age, but I can see 60 on the horizon. My body is starting to tell me that I’m 57. I’m not sad about it, but it is significant. How many years do I have left to effortlessly ride 125 miles per day for 4 days in a row? What might stop me?
3. I’m right where I’m supposed to be. In life. Finally. The last year has been filled with some of the highest highs and lowest lows of my life, but I’m good. Really good. I don’t know if I’ve honestly been able to say that and mean it prior to now.
4. My Dad only brought me into his world. I consciously chose to live in my kids’ worlds instead. Now that I’m an adult, I can enjoy both worlds, and so can they. My dad bought me hunting stuff for my birthday. He liked hunting, I did not. I liked bikes. My kids have bikes, but their bikes were never presents. That’s my thing. I just made sure they always had good, safe ones. Having Blake drive SAG the last 2 years was awesome. He’s not riding, has no desire to, but he gets to live in my world for a long weekend. He gets to fish a little (his thing). He gets to experience me with my friends. My genuine self. Gets to meet and hang out with my friends. And gets to see how good men interact with the world.

Enough touchy-feely stuff, now onto the ride. After waiting out 5 1/2 hours of pouring rain we finally faced the inevitable and rolled out into it.

Starting at 1:30pm only allowed for 70 rain-shortened miles on Saturday. We rode mostly in the rain before, eventually, Mother Nature relented and the rain stopped. Temps slowly rose and the ride was actually pretty enjoyable. Blake did a great job in the Broom Wagon, and after an impromptu stop for ice cream, we were home by dinner time to enjoy Mike’s legendary smash burgers followed by more ice cream.

Day 3 finally brought amazing weather, roads, Kwik Trips, Culvers, and traditional distance: 126 miles and 4,000 feet of climbing. We capped the evening with an amazing French dinner, prepared by Chef Finn.

Our Sunday route put us onto the Madison Ironman course, where we found 50+ riders out training. At one point we stopped to help a woman who’s seat had come loose and was riding standing up. We also came across this young woman. Riding a bike with the seat 2″ too low, unpadded yoga shorts, huge smile on her face, just smashing the hills on pure naiveté. She was strong as Hell, no idea what she was doing or how strong she was. Very cool to see.

Day 4 was a short ride home – only 94 miles. bc had to tap out on Sunday to fly to North Carolina for work on Monday. I had to drive to Springfield, IL for work on Monday night, a 5 hour drive, so I was happy to get home a little early. The weather was spectacular and the miles ticked by pretty effortlessly. We fell short of 500 miles this year, a stat that no one really cares about anymore. After 16 years, with some years being over 500 and a few being under, we’re now running a small deficit – not quite 8,000 miles in total. That used to matter. A lot. As this ride has morphed and evolved, what really matters now is who we’re spending our time with and how. The people we meet, the individual memories we come away with, and even the planning and training (or lack thereof) for the following year. Of course we ride. Normally all day, every day. But it’s the experience, not the miles, that is at the forefront. Next year we’ll likely get all 500 or more back into the schedule. Maybe.

2027 Windy 500 – August 6-9