2021 Windy 500 dates/routes/details…


2021 will be the 11th running of the Windy (10th anniversary). After the 2019 edition, I had grand dreams of making the 2020 version into something huge. As it turns out, that is what spoiled the magic in the first place. 2020 ended up being (because of COVID) one of the smallest groups of riders AND one of the top 3 best rides of all time.

(Lack of) planning is what made the first-ever year the gold standard. We had a mission (idea), 3 planned hotel stops, and UPS boxes en route to all 3. Aside from that, any “planning” that happened prior to launch was subject to change and/or ridicule. No SAG or support, a route that was all but abandoned 75 miles in, and 4 guys with no clue what they were doing. It was spectacular!

Over the years, the ride has grown and grown. Roughly 50 (?) different riders have taken part. Some just once, some two or three times, and others lots more. Mark Lampe has participated in every ride since 2011, bc has been there since the year 2012, but only Chris McArdle and I have covered all 5,089 Windy miles together.

Over the years, the ride grew by word of mouth and at some point, it just got too big. It became more of a guided tour. It’s easy for a handful of dudes to roll into the Town of Nowhere and get an “on-demand” burger and a beer for lunch. It’s nearly impossible with 28 guys unless you have a few hours to spare. Chris and bc spent hours upon hours designing routes and stops because there were “so many people” (an ode to Chris), it became a part-time job to plan and then execute the ride.

In 2019, we came up with the bright idea of limiting the riders to a specific number by using a scoring method. Yeah – that was stupid. ‘Nuff said.

2020 was wide open, and then COVID hit. I had intended to do a “Windy 1,000” for the tenth year. After COVID, we split it into 2 separate 500-mile routes. Yeah – that was stupid. ‘Nuff said.

The Windy 500 will always be the Windy 500. There were a few rules (guidelines really) that we used initially. After a few years, it became clear that spending a few days riding all day with friends and covering (+/-) 500 miles was spectacular. No rules or guidelines needed. This brings us to 2021…

For the 11th ride/10th anniversary, we are still discussing the details. What we do know is:

  • The ride will be 500 miles. Ish. Not 1,000. Ish.
  • The ride will take 5 days. Thursday, August 5 to Monday, August 9. This year, we will be enjoying a celebratory 5-day timeframe with a first-time-ever Saturday “rest day”. Hanging out somewhere all day; swimming, beers, jamming tunes, recovering, grilling out, bonfire and bourbon.

  • Limiting riders to 18-ish. Simply the first dudes with deposits in will ride. Judgment free zone.
  • Rolling hills, no pride-busting Categorized climbs.
  • Probably headed North. Looking to do an Airbnb on a lake for the turn-around day.

More to follow. But if you know, you know. Find the link, pay the deposit, you’re in. There are a few dudes who’ve never done it that would be fantastic to ride with. There are a butt-ton of veterans who’d be awesome to ride next to. Don’t get left behind.

Published by Jason Kayzar

Unprofessional cyclist

One thought on “2021 Windy 500 dates/routes/details…

  1. I’m in for the 2021 Windy 500 goodness. We need to find a better wine bar in the UP though (#1 year vintage selection was dismal). At lest the trampoline was fun on walk to hotel,



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