*The WINDY 500*

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The Annual Ride of Stupidity!

4 days, 500 miles (or maybe a couple more)

“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) … Pretty sure we’ll go North again, may add a day off in the middle to grill/fish/swim/drink beer…

Tentative 2021 dates/routes/details

Beer, Bikes & Miles.  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 thoughts on “*The WINDY 500*

      1. 2013 was Milwaukee to Illinois to Munster, Indiana and back (considerable consumption of 3 Floyds in Munster).

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  1. 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.

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