2020 Windy 500 Wrap-up

This is what 51 years old looks like.

More specifically, this is what it looks like at the halfway point of this year’s ride, with 2 days, 260 miles, and 11,000+ feet of climbing in.

In fact, this is exactly what 51 looks like after the tenth year of this ride.

5,089 total miles. So far.

That’s roughly Milwaukee to Los Angeles, then back to Milwaukee, then back to Los Angeles…

123,162 total feet of climbing (23.3 vertical miles). So far.

That’s the equivalent of Felix Baumgartner’s jump from space back to Earth – but going straight up, not down. Or climbing all 42 floors of the US Bank Center, the tallest building in Milwaukee…

205 times.

This is what this year’s crew looks like, including the breakfast crew and Johnny Croc, our lead-out man:

Let’s face it, 2020 might go down as one of the shittiest years ever in our lives. But this ride might be the only “normal” thing right now, and there was no way I was cancelling.

Ten years after dreaming this up, it’s just a part of life now. For me, and everyone that continues to make it happen. So it had to happen this year.

Day 1

It was weird having such a small crew. Weird, but really good. We normally roll out about 30 strong, including a few dudes that just roll to breakfast with us that first day. We normally have a full-sized Sprinter van, loaded down with bags, bikes, wheelsets, beer, you name it. This time, it was just an SUV with our gear and the bare essentials.

Weather was spectacular, the rollout was uneventful. Unlike having a giant peloton, we quickly found our rhythm this year, and it was on.

Just outside Beaver Dam (home of the Golden Beavers…), bc flatted (1 of only 3 flats on the entire ride) and we rolled into a driveway to get out of traffic. As soon as we stopped, out walks Fred Kaping. Retired Navy Vet, realtor, jack of all trades, and phenomenal home brewer! We offer PBR as payment for blocking his driveway, he returns the favor with Fred Brew – a deliciously smooth 14% ABV homebrew.

THIS is what the Windy 500 is all about. Random acts of kindness. Meeting new people and seeing new things you’d NEVER otherwise experience. We all roll out from Fred’s agreeing that his grandkids are some of the luckiest kids on Earth.

From there, it was a fairly regular roll the rest of the way to our home away from home for the weekend, the Spring Valley Inn. If regular includes a “biker” in a leather vest and boots on an E-bike playing Pantera through his phone…

We did what we always do, offered him a PBR, and listened to his stories.

Then food, drinks, fire & bed.

Day 2:

Rolling hills are supposed to be rolly… Right?

We had some beautiful scenery and some modest climbs, but apparently, Chris thought the best birthday present of all for me (and all of us) was a kick in the nuts:

6,300 ft of climbing with (7) Category 4 climbs. Really? And no receipt with this gift, so I couldn’t even return it. Asshole.

Fast forward to Saturday night – where a bunch of very tired riders enjoyed a delightful 5-star meal of deep-fried fat under the too-bright fluorescent lobby lights of the hotel.

Without Janisch, we all had pizza AND wings!

Day 3:

Another long day in the saddle, but nowhere near the soul-sucking climbing of the day before. Tapped out the day at an easy pace, dodging a few raindrops and falling temps along the way.

What would the Windy be without Mother Nature imposing her will??

More bike riding, PBR stops, etc., etc., etc…

Day 4:

Locked and loaded for the trip back home. Could not have done it with the Brothers Sag – Nick and Jon. You guys are AWESOME. Thank you so much.

That one time when Dino forgot he wasn’t at ToAD…

Finally some Mexican!!!! Beef tongue with habanero sauce. Least calories consumed ever on this year’s ride, but I still managed to gain 6 pounds??

We’re all getting older, but I’ll do this until I die. It’s become such a part of me, that I can’t imagine NOT doing it.

The beauty of the Windy 500 is not the ride. It’s not the “500 miles in 4 days”, although that’s always fun to tell people – especially non-cyclists. That’s just the road map. The true joy is the journey – all the moments in-between. There have been countless memories over the past 10 years. Sure, a few of them involve Mt Kickintheballs Hill, and wanting to heave up your spleen, but almost all of them have nothing to do with bicycles.

For me, this was never about riding bikes. It was about adventure. It was about people. And the ride has never disappointed. Yes, some years have been better than others, but after 10 years I wouldn’t change much.

I can’t wait until next year, and I can’t thank every single friend who’s ridden next to me enough for all of these memories.

You guys are the best.

See you in 2021.


Published by Jason Kayzar

Unprofessional cyclist

One thought on “2020 Windy 500 Wrap-up

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