*The WINDY 500*

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The Annual Ride of Stupidity!

4 days, 500 miles (Or maybe a couple more. Or less.)

“I love to travel, but hate to arrive.”

~ Albert Einstein

2011:

Milwaukee to Iron Mountain, MI to Milwaukee – July 15th – 18th, 2011

2011 Ride Report

2012:

Milwaukee to Winona, MN to Milwaukee – August 3rd – 6th, 2012

2012 Ride Report

2013:

Milwaukee to Illinois to Indiana and back – July 26th – 29th, 2013

2013 Ride Report:

2014:

“Legacy Route” Milwaukee to ‘da U.P and back – August 1st – 4th, 2014

2014 Ride Report

“The new normal” Milwaukee to Escanaba, MI, and back – July 31st – August 3rd, 2015

2015:

2015 Ride Report

Deja, Deja Vu route: Escanaba and back – July 30th – August 2nd, 2016

2016:

2016 Ride Report

Back to the 2012 route: Winona, MN and back – July 28 – 31, 2017

2017:

2017 Ride Report

Deja, Deja vu: Back to Winona in 2018 – August 3 – 6, 2018

2018 Ride Report

2019 Milwaukee to Green Bay, with 2 out & backs (something old, something new)

2019 Ride Report

2020, the 10th Annual Ride of Stupidity – the COVID year

2020 Ride Report

2021 (10th Anniversary, 11th ride) … North again, added a day off in the middle to hang out…

2021 Ride Report

2022 – The Goldilocks year – just right!

2022 Ride Report

2023 – Year 13 – more of the same, please…

Ride your ass off – laugh your ass off.

Email me for details – jasonkayzar@gmail.com

2013-07-28 19.19.09

2013-07-27 16.50.33

Windy 500 2015 (62)

W5002014

18 responses to “*The WINDY 500*”

  1. Russell Avatar
    Russell

    A real man would do this in December. When do we leave?

    Like

    1. Jason Kayzar Avatar

      Oh, you’re thinking of the Icy 1000…

      Like

      1. chaosupfront Avatar
        chaosupfront

        2013 was Milwaukee to Illinois to Munster, Indiana and back (considerable consumption of 3 Floyds in Munster).

        Like

  2. Rob Avatar
    Rob

    Someone should mention this type of thing a little more than 2 weeks in advance! Just two days ago I signed and paid for another event to do the weekend of this event. And to think this is the year that I’m a roadie too and I can’t do this; Oh well, maybe next year.

    Like

    1. Jason Kayzar Avatar

      Dork. It’s been posted for 2 years!

      Like

  3. chaosupfront Avatar

    I like for biking they show pizza, Cherry Garcia & pints of beer. You got to love it.

    “Let Them Eat Fat” NYT July 29, 2012 Magazine: http://www.nytimes.com/2012/07/29/sports/olympics/why-some-olympic-athletes-need-to-gorge.html

    Like

  4.  Avatar
    Anonymous

    2013 Almost the most painful fun I ever had. Long Live PBR’s

    Like

  5.  Avatar
    Anonymous

    sup

    Like

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