2023 Windy 500 wrap-up

“Knowing yourself is the beginning of all wisdom.”  ~ Aristotle 

Early on, this was just the “Ride of Stupidity”. A handful of dudes covering as many as 160+ miles in one day, and then repeating the cycle for 3 more days. Initially, the ride was open to anyone who was dumb enough to participate. We didn’t necessarily take on strangers, but we didn’t exactly pre-screen the candidates. (Ask Steve Sarver about the year he showed up in the driveway 10 minutes before launch and everyone said “…who’s that guy…?”)

Some of the the earlier iterations were fraught with frustrations because the group was such a mixed bag of riding skills and abilities. It’s one thing to do a solo 100-mile charity ride at 15 mph, but it’s a whole other thing to do 500 miles in 4 days riding 2-up at 20-24mph on the flats, and staying together on the hills. More than a few guys were ground to a fine powder by Day 4 over the years. And guys who’ve raced criteriums for years, 6″ from a wheel on all 4 sides, at 30+mph, were frustrated with the accordion effect of inexperienced group riders hitting their brakes uphill (true story). As the years ticked by, what was once a tiny group of 4 dudes with no clue and no support, became a rolling circus of sorts, almost 30 guys thick, requiring professional-level planning and logistics, and it ceased to be much fun.

And then – COVID happened.

The world crawled into a dark hole and turned out the lights. All was silent except for our small group of guys – determined to live life again, even if only for 4 days. There was no longer a waiting list, or a roster of 2 dozen plus. In 2020 we went back to less than 10 riders, and it was spectacular! McArdle and bc chose some routes that were not only beautiful, but really challenged the group physically without tearing us apart. At the end of each day we were spent, but happy. The local bar/restaurant was oblivious to the world outside and we gathered with the mask-less locals like time traveling bandits. We had re-discovered the true soul of that original Windy year, and it was time to rebuild.

Admittedly, 2021 was a stutter-step. We again tried to serve the needs and wants of the masses with a vanilla ride that lulled me to sleep. It was still fun, and I enjoyed it, but I thought it was boring and predictable. It didn’t recapture the magic of that previous year, and I felt like I finally knew why.

Let’s be honest, Year One was a mess. But it was a beautiful mess. There was some planning, but not enough to really address all of the issues that we encountered. At the end of each day, we had a clean bed and a shower. That was guarantee #1. And that was the only guarantee. The rest was a lot of “rolling the dice” and other gambling analogies. But, it was an adventure, in the purest sense of the word. While we didn’t need to “lay it all on black” again, we did need to rekindle that spirit of freedom. So the powers that be (bc, McArdle, me, Mike O.) with input from a few others, burned the Windy rule book and began re-writing it. No more “surprise” pre-planned tourist stops. In fact, less stops. Meaning, less Kwik Trip stop-for-way-too-long while someone debates the merits of salted nut rolls vs. grab-n-go sammiches, and more stop and stretch in someone’s front yard in Bumfuckville, USA. Less pre-planned, foot by foot, 125 mile routes, all pre-loaded into our computers weeks prior to launch. We needed to get to get to our base camp and back, and let’s just figure the rest out on our feet. In fact, if we cross a state line, so be it. If we don’t who cares? And finally, accommodations. Year One was a few crappy hotels. Over the years those places were sometimes much nicer, sometimes crappier. But they were always hotels – 2 guys to a room, meet in the lobby or the pool area at night and compete with screaming kids and the echo chamber effect of tile everything, hot-as-balls pool common areas. What we needed was our own place…

May I present to you, 2022 the Year our Lord. Aw, snap – we figured it out!

Finally, the 13th annual running of the Windy 500, 2023.

We didn’t try to re-create anything this time. We didn’t try to re-capture anything either. We started fresh. As McArdle said, we just focused on what WE wanted to do with 4 days off work and on bikes. And it was AMAZEBALLS!

Like any other year, the witty banter and nervous excitement ramps up a few weeks before launch. Admittedly, it’s not like in years past when 20+ dudes were practically peeing their pants for two months prior like it was 11:55pm on Christmas Eve and we were 8 years old, but it was banter nonetheless…

At roughly 6:30 a.m. the the day of launch, the texts fire up: people on their way, arriving, etc., and the show begins. The SAG wagon sits empty, ready for the load-up, and riders begin pulling up. Some ride in, some drive in. Slowly and methodically, my driveway becomes the departure area for Train #13 at Grand Central Station. Wives dropping off husbands, kisses goodbye, scurrying off to their own weekend adventures. Over-caffeinated middle-aged men in too-tight Lycra, anxiously pacing the driveway, waiting for the checkered flag. Eventually, the van is loaded, all of the last minute bathroom visits are concluded, the SAG driver settles in, and we roll out.

The rollout – 364 days of planning and anticipation turn into infinite pedal strokes and warm sun on our faces. Out of the driveway, up the hill, checking to make sure everyone’s in, Blake tapping out, checking for the SAG van, settling in…

Over the next 10, 20, 30 miles, everyone begins to define the group’s rhythm. It’s not a dictated pace, it’s a mash-up of the individual contributions. At first, it’s clunky – too fast up the hills, too slow up the hills. Not fast enough on the descents. But eventually the pace melts into a warm gumbo that seems just right. It’s a casual cadence that requires some effort. And just as it locks in, we stop for breakfast.

If you’ve been paying attention for the past 8 years, then you know where we are. Alma’s Cafe in beautiful Allenton, WI. OK, maybe Allenton is just another crappy farm town, but Alma’s is the shit. They’ve been rolling out the red carpet for us since 2016, and we’ll probably never not go there! Coffee, hash browns and fat egg, bacon, sausage and cheeeez sammiches by the dozens await. It’s a team effort, and we do our best to smash them all.

Then with bellies adequately filled, it’s out to the parking lot to immediately climb a hill. Never fails, all the best food stops are at the base of a hill. We say goodbye to the Breakfast Club riders and begin the real ride.

Someone had to tell Mike and Pat that this was serious business. Stop having so much fun. Dammit. You too Leach!

And the group rolls on…

Much of the early climbing every year is just getting away from my house. Heading West or North, our usual routes, takes us into the country and the rolling kettles and hills of Southern Wisconsin. This year, the stars aligned. We had no mechanicals, and just a couple of flats. Slow leaks really, but nothing that took us off our game. We were free to roam the countryside for as long as the group dictated before finding the next Kwik Trip or shaded front lawn to park at for a few minutes.

Not only were the guys this year some top notch dudes to spend time with, they were also very capable of keeping a moderate pace throughout the day. The slower guys took it up a notch and the faster guys took it down a notch and we found a great medium-speed pace that fit us pretty well for all 4 days. Along the way we were able to check off most of the Windy favorites: A&W Root Beer, Kwik Trip, random strangers’ yards, etc.

All in all, the day was fun, uneventful and went by relatively quickly. The weather was spectacular, and, despite averaging almost 500 watts, I felt fresh as a daisy when we rolled into the best Windy 500 shack ever created…

Behold – the most awesome place we’ve ever stayed. Proof that someone did something right at least once:

As bc likes to say, this place did not suck. We were the very first group to stay in this brand new construction, VRBO shack on the velvety Lake Wagena. Amazing place, amazing food – prepared by our own riding chefs – starlit evening cruises on the pontoon, and bonfires before bed.

Day 2 was the kindest, gentlest day. 126 miles, 3,661 feet of climbing, casual pace. We headed north from Wild Rose along the deserted back roads of Central Wisconsin. Traffic was at an extreme minimum and the miles ticked by almost effortlessly. At times it literally felt like we were riding through some abandoned golf courses.

I would have really enjoyed myself if not for the terrible traffic, weather, scenery, and riding companions…

First stop of the day was hampered by a parade at the exact moment we swung onto Main Street, Shitdickville. You cannot make this stuff up. Fortunately, we waited it out at a tiny diner that served the best quiche known to mankind.

bc challenging the jockey to a footrace, both wearing horseshoes. OR he was comparing unit sizes. I was too far away to hear the actual exchange.

A quick word about this year’s Rookie – Sam Janisch. In the days leading up to this year’s ride, I talked to a number of non-cyclists about the ride and the riders. I mentioned that this was the first time we’ve ever had a father/son duo. There seemed to be some concern about the young lad keeping up with the seasoned riders. Unlike the geriatrics of the bunch, Sam spent some time racing on the Pro circuit in Europe. Quite recently. So my concern was that we would bore the shit out of him with our “chat pace” riding all day. Unless Sam is the world’s best actor, his old soul actually fit our group like a glove. He was happy to take pulls into the wind, but also just happy to be riding at any pace. And seeing him riding shoulder to shoulder with his Dad most of the time was just awesome.

I’m not crying, you’re crying!

A younger, more innocent and unmoustachioed Pro Sam

Back on the road… or gravel. Up Nort’, you get what you get. I’m always happy to launch into some gravel, especially on the 30c tires I rode this year. The roads were generally in pretty good shape and not a car to be seen for miles at a crack.

A quick stop at bc’s cabin, with ice cold refreshments provided by his lovely wife Pam, and we were back on the road.

If this is your idea of a good time, you were already part of our group… There was a lot of disbelief about our good fortune all weekend. A lot of “I can’t believe how awesome…”. (And that was just the talk about me).

Here, Mike offers encouraging words as I poop myself. Or something. Not sure what was going on in this pic:

The food we find on the Windy is always legendary. It’s usually Mexican, but this year the theme that materialized was “Porkopalypse”. I think we enjoyed pork for breakfast, lunch and dinner for 3 months straight, even though we were only gone for 4 days.

My weight gain this year over the 4 days was: 8 pounds.

Lunch today was… pork sammiches. I gave the bar owner a serious myocardial infarction when I dumped an entire container of the “Intense Pig of Death” sauce over my lunch. I had to ask for it twice, because apparently they keep it in a vault next to some uranium. It did NOT kill me, but later that day I found myself sweating much more intensely than the others…

More riding, more swimming, more boating, and more awesomeness ensued. End of day, wait for the next. Begin again at daybreak.

More amazing roads to ride and riders to ride them.

Mandatory Kwik Trip stops each day kept us fueled up. Nothing but the finest processed and over-salted foods for these race-tuned machines!

The Windy is actually my birthday ride. But it’s also Bill Finn’s birthday, and this year Bill’s wife contacted me pre-ride to help with a covert mission to spread joy and happiness to her husband. I chose to accept the mission. My role was easy – just give her the location of our HQ, and keep her updated as to our whereabouts during the day. Kirsten drove all the way up to Wild Rose while we were out and put out a surprise for Bill when we rolled up:

We celebrated Bill’s birthday the best way we knew how: by treating it like every other day of the Windy. It was really hard to pack any more fantasticality into each day.

Fortunately or unfortunately, there’s always got to be a Day 4. Sad because the Windy is winding down. Happy to be heading home to family. Some guys are still fairly fresh while others a bit road-worn. We dial the pace down a notch and enjoy our last day on the road together.

The day rolls along and sights begin to seem familiar as we get closer and closer to home.

Eventually, we ride right back into my driveway. Sweaty hugs and high fives all around, a group pic, and everyone starts packing up. It’s all part of the routine. Inevitably, someone leaves something at my house, like a desperate first date hoping to find a reason to return and pick up where they left off. But sadly, it’s over. For now. 2024 planning and preparation starts immediately.

I think Lex found Bill’s bottle opener…

So, another year comes to a close. I will ride this ride until I’m dead, and then maybe 3 years after that. It’s such a part of my soul that I cannot imagine a summer without it anymore.

I’ve been fortunate enough to spend these 53 days, over 13 years, riding 6,549 miles and climbing 156,639 vertical feet (almost 30 miles straight up) with some of the best guys on Earth. I love you guys, thank you all for coming along, and I will cherish your brotherhood for all of my life.

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One response to “2023 Windy 500 wrap-up”

  1. chaosupfront Avatar
    chaosupfront

    Beautiful wrap-up Jason. I will be back & thousands of Kudos to you & all the Windy 500 knuckleheads. AirBnB sure Trumps (pard

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