…Faster than Last

Endless miles of rollers, Olympics, bikes, and brothers from another mother.

“Mountains should be climbed with as little effort as possible and without desire. The reality of your own nature should determine the speed. If you become restless, speed up. If you become winded, slow down. You climb the mountain in an equilibrium between restlessness and exhaustion. Then, when you’re no longer thinking ahead, each footstep isn’t just a means to an end but a unique event in itself. This leaf has jagged edges. This rock looks loose. From this place the snow is less visible, even though closer. These are things you should notice anyway. To live only for some future goal is shallow. It’s the sides of the mountain which sustain life, not the top. Here’s where things grow.”

Source: Zen and the Art of Motorcycle Maintenance

So, it’s been a few months now since we rolled. This wrap-up post has been sitting, half-finished, on my laptop since September. For reasons I will explain, it gets tougher and tougher to summarize the ride every year.

It was amazing (– how’s that?). It usually is, even in some of the not-as-awesome years of the past. Each year, because of the nature of the ride, I equate the 4 days to personal growth, or regression, based on whatever is happening in my life at that moment. Therefore, when I think back on those 4 days, I don’t really think about covering 500 +/- miles on two wheels, but rather – what issues did I work out in my head over those endless hours on the road? Some years have been very tough. Wearing a fake smile and wanting so badly to really enjoy the moment, but feeling trapped in my own skull, unable to get out of my own way. Others have been more liberating – the stars aligning during a partcularly high upswing in life, and I was able to breathe out just as much as I was breathing in. I can’t speak for the other guys on the ride, but I imagine that the ones who always show up have similar M.O.s. Yes, they ride bikes all day over sometimes challenging terrain at sometimes challenging paces, but perhaps they too do so to exorcise some mental demons and clear their heads a bit.

At one point in life, I had the honor of working with a lot of military veterans. We sold and serviced industrial equipment all over the globe. Vets could jump on a plane with a Dollar Store screwdriver, land in Dubai, find their destination, stay for 2 weeks, fix the equipment and head home. They taught me a lot about self-reliance, toughness, and respect. They also taught me a new term – “liberty risk”. A soldier is considered a liberty risk when they are deemed likely to engage in behavior that could lead to trouble or disciplinary issues when granted freedom from duty. Meaning, send a young kid fresh out of a stint in the military to Dubai for 2 weeks with no supervision and a corporate credit card and don’t be surprised when he’s out getting shit-faced, hanging out with hookers and doing God knows what else at night.

Over the course of the Windy, I had become somewhat of a liberty risk. Even though I knew I had to wake up each day and ride 125 miles, I would often drink too much on the rides. I never let it affect my ability to ride, or even ride strong, but it was always there. As the years wore on, I was screwing myself further and further into the depths of dispair personally, and the 4-day getaway was my excuse to “have some fun” with my friends. There were a couple of years where I dialed it way back, and a year where I was completely sober, but I still hadn’t dealt with the reasons that I was so unhappy. So, eventually I’d ramp it back up and find myself in that comfortable misery again.

I’m typing this because it’s a kind of therapy for me. It’s been a few years now since I had a drink and my life could not be more amazing. The past 2 Windy 500s were all about the ride, living in the moment, and spending good quality time with a group of guys that I really love to be with. We laughed at stupid shit, talked about real life stuff, and ate all of our meals together – like a family.

That’s what the spirit of this ride was always meant to be, and for me the past 2 years have been an unbelievable leap forward. The Windy finally has it’s soul back. The details now take care of themselves, and we’re not trying to craft something new each year. It’s become what we (collectively) all wanted and needed it to be for ourselves. And – bonus – we get to ride our bikes all day. That is why this ride holds such a special place in my life. I need to do it each year. I can’t imagine not doing it ever, even though I know that sadly someday that time will come.

So – I will recap the ride below, but mostly with pics, because I can only speak for myself about the experience, and I’ve already done that.

~Jason

They say you can choose your friends, but you can’t choose your family.

First off, who is “they“? They are wrong. (“Thine”, “Thou” are wrong?) I have had the good fortune to hand-pick the people I call my family. And I’ve been lucky or blessed enough for them to do the same. Starting with my wife. Then our 2-person family got a dog and created a few more humans to help fill our house. And now I have all my Windy brothers too. Unlike biological brothers, these friendships are built on shared experiences, mutual respect, and a deep understanding of each other’s strengths and weaknesses. I have laughed until I cried with these guys and cried until I laughed. Over the past 14 years we’ve ridden our bikes 7,000 miles together on this ride, (and countless additional miles on other rides). Riding 7,000 miles is roughly equivalent to traveling the distance from Los Angeles, California, to New York City and back, plus a bit extra. The origin of this ride was a replacement for NOT riding my bike cross-country back when I was 40. Now, we’ve achieved that goal more than 2 times, and we’re still going. We’ve climbed over 32 miles straight into the sky together, and descended that same 169,605 feet of elevation at speeds of more than 55 miles per hour. Every Windy has started at the end of my driveway, and ended right back there a few days later. It’s the closest we can come to being 13 years old again – setting out for all day adventures on our bikes. The best part back then was the sense of freedom, just pedaling away with the wind in your face, not a care in the world except making it home before dark. Or fast forwarding to 2024, making it our VRBO before dark. And we still do it for the same reason.

The 2024 Windy 500 in words and pictures…

It gets harder and harder every year to describe this ride – not because it’s not awesome, but because it is. It’s kind of like eating your favorite meal at your favorite restaurant once a year for 14 years. The first time – indescribably delicious. The second time – just as good as you remember. The 14th time? Yep, amazing. Just like last time. Not much more to say.

Onward.

Our small group rolled out just after 8:00 am on August 2. Our Day 1 destination this year was Sheboygan Falls, with a West Bend breakfast stop. After X number of years, the crowd favorite breakfast spot, “Alma’s” in Allenton, closed its doors and we were forced to look elsewhere. bc found us a great little diner in downtown West Bend that was last cleaned in a year that preceded my birth. Unfortunately, they knew how to TAKE the reservation, but did not how to HOLD the reservation. Probably best, since we’d have all left with typhoid fever or something worse.

So we rolled on. Eventually, we found a weak excuse for breakfast at a gas station (shocking, I know). Eat Trash was on the menu that day, Ride Fast was not. But everyone found a luke warm sammich or nut roll or something to keep them going and we got back on the road.

And the ride continued. A very humid and somewhat hot day presented definite energy challenges for the group. To add to the less-than-perfect conditions, we faced an almost constant Northeast headwind, and we rolled up and over about 4,000 feet of climbing all day. Many of the hills were rollers, but there were a few short, steep efforts that taxed about half the riders. Any of these factors alone would not have presented much of a challenge, but the combined force of all 4 for an entire day seemed to sap the group’s spirit.

This is by no means a race. Contrary to what my non-bike-riding friends seem to think about a 500 mile ride, we do roll at less than what I would consider a “chat” pace. There have definitely been times when the pace was hotter, especially when we were younger and the make-up of riders that particular year was dominated by guys who had raced their share of criteriums. But this ride has really mellowed into a “ride”. Having said that, this year’s pace was the slowest on record. That’s neither good nor bad, just a fact. And slower speeds dictate a completely different style of riding. I had planned to ride my single speed for all 4 days, but after Day 1, I realized that I couldn’t ease up hills with the group using 52×16 gearing, so I opted to grab my spare (geared) bike from the SAG van for Days 2-4.

Mike O. sponsored an Easter Egg hunt at Mile Marker 77, but no eggs were found. Just nuts.

A couple (2) flats was all that registered in the “Mechanical!” category for all of the miles, with both coming on the front end of the weekend. There’s a definite difference with most guys running tubeless setups now.

Day one is always the settle-in day. Imagine a silent rave, where everyone is listening to their own music instead of the same track. That’s the start of the Windy. Everyone rolling out at the cadence that they naturally default to, and then trying to adjust to everyone else’s. Clusterfuck is a word that comes to mind, although it’s not really that bad. It just takes a few miles for everyone to settle in. By Day 4, the pace is a never-ending beat in your head, and you can ride at the group’s pace without a second thought or a glance at your computer.

Unfortunately, prior to August, our 4th Musketeer, Mike O., tried to ride his bike directly through the Earth and broke his hip, but not his spirit. He took one for the Team, and drove the sag wagon this year.

I have never driven a sag wagon. Mike had never driven a sag wagon. Driving a sprinter van all day behind a group of middle-aged men going 20mph sounds as amazing as shaving with a cheese grater. But our man soldiered on and made an amazing sagman! He also vowed to make it a one-and-done experience.

P.S. – the most scenic, spectacular routes this year were served up by the legendary, but absent, Sam Janisch. Mike proudly drove the Sammobile for the entire duration. If all goes well, and the juju has rubbed off, Mike will be 125 pounds next year, sport a porn stache, and be fast as shit. If Sam doesn’t return for 2025, we will blanket party his ass.

The day ended at our base camp chateau in Sheboygan Falls, 109 miles from home, and just 100 vertical feet from Dairy Queen. Age and wisdom have taught us that staying with Tom Bodet, or his meth head cousin, for 3 nights is not worth the pennies saved or diseases acquired. This is an actual photo of the worst hotel in America, which we stayed at in one of our trips to Winona, MN. Yes, they were selling used wheelchairs AND organs in the lobby.

For the past few years, we’ve upped the ante and sprung for a nice VRBO. Game changer.

Day 1 left no gas in the tank for the arduous 100 foot climb for frozen treats. But Day 2?… Note McCardle’s Bruce Pagel impersonation – SAFETY FIRST.

Day 2, 3, 4…

After a real night’s sleep on a real bed, Day 2 was a 123 mile loop North to to Denmark (Wisconsin).

Pat and David found new and innovative ways to keep Leach cool.

Day 3 was another out and back, this time through Kiel and more Westerly before looping back to Sheboygan Falls. Amazing scenery and endless rollers. Or was that Day 2? Day 4? Does it matter?

Along the way, I tried my hand at mini golf…

The new rigs, Sam’s van and my bike, were flawless all weekend.

And Janish was always there to help us communicate with American Sign Language…

The scenery was absolutely beautiful, with some areas reminding me of the Driftless routes we have taken in years past.

Day 4 was a 118 mile zig zag home through more beautiful, rolling Wisconsin backroads.

There are lots more stories, and a few more pictures, but you kind of had to be there.

Next year’s plan will slowly take shape over the winter and early spring and we’ll be back on the road before we know it for the 15th running of the Windy 500.