“The best thing one can do when it’s raining is to let it rain.” – Henry Longfellow

I ran into Lex at Colectivo a few weeks ago, and he gently reminded me that this wrap-up has been sitting in my to-do box for way too long. He’s right, but I needed time to think through my commentary like every other year. And, like every other year, there’s been a lot of “stuff” going on. This week, Mike reminded me about this wrap-up. Again.

The Windy means more to me than most people will ever know or understand, so the process of reviewing and writing about it holds a special place in my heart. Whether anyone reads this or not, my recap has to be an honest assessment and that’s a process that can take some time to get right.

So here goes… The 12th annual Windy 500.

This one was definitely in my top 3 of all time. It lacked all the stuff I’ve come to dislike about the trip but included much of the heart and soul that we’d been missing from the past few years. Short on mileage and long on experiences, 2022 was the perfect mix.

The rules of the Windy have gradually and deliberately been abandoned over the years as the ride has evolved. In fact, we’ve broken all three at one time or another:

  • Must ride 500 miles
  • Must cross a state line
  • Must be completed in 4 days

The riders have evolved (read: aged) too. Which is just fine by me, since I’m one of them. What started as a crazy idea with next-to-no planning has turned into an annual event that I look forward to almost more than any other.

When initially planning this year’s trip, we dug deep into the experiences of the past to try to (finally) figure out where the secret sauce really comes from. Is it the route? Is it the challenge? The riders? The weather? Yes to all of the above. So ultimately, the answers had to come from what the ride wasn’t.

The Windy 500 is not a guided tour. We had been slowly adding stops and “surprises” along the routes until it had eventually morphed into something as predictable as a ride on the Zoomobile. “…coming up on your left you’ll see Monkey Island…”. This year we didn’t even know where we were going on Day 2 or 3. McArdle and bc (with help from others) plotted out the next day’s route at the kitchen table before bed each night.

By the way, the kitchen table is something we never had before. This is not a ride for the pampered glamper. While we’re not carrying tents and backpacks, we’re also not going to look for bougie hotels anymore. This time, we booked a VRBO that slept a big group. And while the sleeping arrangements were not ideal after long days in the saddle, the vibe was perfect. Unfortunately, some got comfy beds while others got terrible beds/couches to stretch out on after 100+ plus miles. But everyone sharing one house was exactly what had been missing post-ride. In 2023 we’ll again go the shared house route but we’ll definitely look for better sleeping accommodations. Having everyone together at night made for some of the best brotherhood, conversations, and fun of any year I can remember.

Because our VRBO was a condo, we got the added bonus of having a bachelor party group for neighbors. While our 40-60+ year-old group was content to chill and hit the hay early each night, “Moose” and his 20-something Illinois dumbassery crowd next door provided endless entertainment for us.

The Windy is not a ride for the casual cyclist. There were a few throat punch days in years past that really tested the group. And I was a huge fan of those days, for reasons I’ll explain later, but this ride is not the time or place for appraising individuals’ mental and physical limitations. It’s a time for community, camaraderie and shared experiences. Should there be a tough climb or two? Hell yes. Should there be full days of testing the limits? Absolutely not.

The Windy is not for the solo rider. Over the years we’ve included several riders who log a lot of miles, but never in groups. They were “Windy-curious” outliers who are strong riders but couldn’t or wouldn’t hold a wheel. They never struggled to hang in, even on the toughest days, but their personalities and/or lack of group riding experience put them at a big disadvantage. They also put others on edge, even at risk, by not being comfortable riding at speed in tight groups in maybe less-than-ideal conditions.

The Windy is not something you show up for and are escorted through. Year one was a colossal disaster in some respects. While the memories of that year have been romanticized over the years and many of the bad parts have been forgotten, we just about killed one rider. We ran out of sunlight on Day 1 and rode almost 40 additional unplanned miles, testing everyone’s limits. We had no backup plan. No support. No tour guides. But it was fucking awesome. By comparison, last year was so scripted that we could have printed glossy brochures and charged a fortune to anyone that was only there to brag about it online afterwards. For me, it sucked.

This year, we finally made some decisions with our hearts, about what we wanted to spend 4 days doing. The “we” is bc, McArdle, and me, but also some of the veteran riders who have the same passion for this ride and want the same shared experiences (Lex, Mike, Finn, etc.). Here’s what we did:

Day 1: A small group again. By design. Gone forever are the days of almost 30 people rolling out of my driveway. Not my monkeys, not my circus. McArdle & bc wisely asked a few local dudes to roll with us to breakfast again. It’s awesome to share the excitement and workload for the first 35 or so miles. Once we get our bellies full at Alma’s, we say our goodbyes to the morning guys and drop the Space Shuttle booster rockets to continue our journey unaided. Speaking of “unaided”, Blake continued his tradition of giving us a terrible lead out, then tapping out a mile into it…

Obviously, not all of the Windy traditions need changing. Alma’s has become our go-to for Day 1 breakfast for years, and it would be hard to top their food and hospitality. Most riders fuel up a little before launch from my house (or their house), and then have the perfect amount of hangry 35 miles later. We crush gallons of coffee and mountains of egg sammiches and then begin the first of many eat-then-climb segments in our too-tight pants.

The Windy 500 is about 2 things: riding bikes all day long, over a long weekend, and spending time with friends I love and respect. Everything else is just details. Every year has always had some of those 2 things, but definitely not always in the right amounts. 2022 was finally just right. No stress, no drama, no rules. In fact, we didn’t even hit 500 miles, but no one cared. The Windy has now chalked up 6,0561/3 miles (so we still have 561/3 miles of cushion). We’ve also racked up 144,691 feet (27.4 vertical miles) of climbing, which puts us just shy of scaling Mt. Everest 5 times from sea level. It’s been a hell of a ride so far, literally, but there is nothing left to prove to anyone. I think that concept finally sank in this year (for me).

As much as my romantic vision of Year One was about adventure, it was also about the insanity of it. I took great pride in explaining to someone that does not ride bikes or maybe rides 3 miles on an old Schwinn once every 5 years, that we left Milwaukee yesterday, and we’re in Iron Mountain, Michigan today. I proudly wore that badge of honor/nut-baggery for all to see. It meant something to ME, even though I now realize that it meant nothing to anyone else. I had something to prove… to someone. So, in some years, we collectively challenged ourselves to go faster. To climb more. To bury the weak. And we did.

And it meant nothing to anyone. But it did alienate people, and make them wish they hadn’t chosen this stupid adventure. And for that, I’m sorry. I now realize that the Windy started as a way for me to exorcise some personal demons. To prove myself to no one but myself.

Thankfully though, this year seemed to start on a lighter note for me. Lighter physically, literally, since my broken jaw had been wired shut for 2 months until just before we rolled out. I hadn’t been able to eat, or breathe through my mouth for the entire Summer and had lost a lot of weight. But mentally, I felt like something was changing too.

This year I really enjoyed the ride. From the front, the middle, and the back of the pack. And I had nothing to prove. I was in great shape: too thin (30 pounds lighter than my COVID high), and ready to race the 153-mile Gravel Worlds on my singlespeed 2 weeks later. I didn’t need to turn myself inside out, proving how fast we could paceline to the hotel. I didn’t need to catch Bill Davis all the way from the back of the pack as he jammed up the biggest climb of the weekend. And so, as I passed everyone and got to within striking distance I finally realized the stupidity of what I was doing. So I backed off a bit and followed his lead over the top. Could I have caught him? Who needed to know? No one. Who cared if I could? No one. Not even me. And that’s when things finally clicked for me. We all rode together this year through some of the most beautiful roads we’ve seen over the past 12 years. The scenery was spectacular, and I enjoyed every second of it.

FYI: McKinney is very picky. He likes “American Food”.

Day 2: While some awoke feeling well-rested, others were still a little tired from our sleeping arrangements. I was in a top bunk on the second floor. The tiny sheets didn’t really fit the tiny mattress, and the summer heat and lack of airflow that high up made me consider sleeping in a nice, cool dumpster somewhere for night two. Meanwhile, the A/C in the basement was blasting harder than AC/DC in a ’76 Camaro. We had to open the freezer doors to warm the room up. Breakfast was whatever we had in the kitchen, followed by whatever they had at the Kwik Trip a few miles away.

From there we rolled out and found some more beautiful roads and scenery and even a little gravel.

For reasons we may never know, the day and the route seemed to really stretch us out. Maybe it was the crappy night’s sleep, or maybe we’re just too old for this. Every minute on the bikes was great, but you could feel the energy leaving the group as the day went on. The route we had picked gave us just about a Century – with options. One of those options was the spectacular outdoor pool (a Windy first), and without hesitation we all chose it. Our day ended far short of the normal 125 miles, and no one cared.

OK, maybe it wasn’t spectacular by “pool snob” standards, but it was definitely spectacular by sweaty, tired, middle-aged dudes’ standards. Note – adding “outdoor pool” to the 2023+ mandatory items list.

Once everyone dried off and cleaned up, we walked the 4 or so blocks to downtown Wisconsin Dells for another mandatory item: Mexican Food. We were shocked to find that the hottest item on the menu that night was the birthday boy – Bill Finn!

Our lovely waiter took a fancy to Mr. Finn, offering him a personalized Birthday greeting with optional personal contact information hidden on the backside… And yes, I just said “backside”.

Sadly, Mr. Finn went home with the exact same number of men he had arrived with.

Day 3, the dreaded shit-storm day: Just like Celine Dion’s heart will continue to go on, it WILL rain on the Windy. And, on Sunday, rain it did.

But, that’s just part of the ride – so we rolled out into it.

Apparently, Bill even found a place to wash his hands.

Doin’ work.

We enjoyed some of the finest gourmet race fuel any Kwik Trips had to offer during the day each day:

At night, more walking and eating. More route planning and chatting. More laughing. And less stress.

Day 4: Heading home. Aside from really bad headaches that lingered after my broken jaw had healed, the ride went off without a hitch.

For the group – a couple of flats, no major mechanicals, no distress calls. In fact, no real hiccups at all. And the best part of all of it was the absolute “unplanning” that occurred each day. Stop when we stop. Go when we go. Take it all in. “Sop it up” as Lampe would say.


Then it stops. We hug and begin to assemble our things, and the world begins to seem still and lonely and odd. Eventually, all of the cars cluttering my driveway for the past 4 days drive away – inevitably leaving random tubes or pumps or gloves in my garage, and the world is quiet. We all go our separate ways and melt back into the real world. Work the next day is a barrage of random text messages that no one else would understand but manage to make everyone in our group chuckle:




“Pop Tart!”

And the planning for next year begins...


One response to “2022 Windy 500 wrap up”

  1. chaosupfront Avatar

    Splendid 2022 Windy 500 recap Jas


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