Category: Windy 500
Every Windy 500 ride report since 2011. The annual Ride of Stupidity: 4 days, 500 miles, no support, starting and ending at the end of Jason’s driveway in Brookfield, Wisconsin.
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Windy 500 – Year 15: When the Wind Doesn’t Fight Back
Every great story needs a demon; an anti-hero. In 2011, ours showed up in full force: flat tires, wrong turns,… READ MORE
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2024 Windy 500 wrap-up
Endless miles of rollers, Olympics, bikes, and brothers from another mother. “Mountains should be climbed with as little effort as… READ MORE
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2023 Windy 500 wrap-up
“Knowing yourself is the beginning of all wisdom.” ~ Aristotle Well here we are – Year 13 of this thing… READ MORE
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2022 Windy 500 wrap up
“The best thing one can do when it’s raining is to let it rain.” – Henry Longfellow I ran into Lex… READ MORE
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2021 Windy 500 wrap up
“Die first. Then you can go about the business of living.” ~ Ekhart Tolle Well, here we are. Year 11.… READ MORE
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2021 Windy 500 dates/routes/details…
All, 2021 will be the 11th running of the Windy (10th anniversary). After the 2019 edition, I had grand dreams… READ MORE
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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… READ MORE
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2019 Windy 500 wrap-up
511 miles. 10,613 ft of elevation. 4 days of awesome. That’s the facts. Now the fluff… The Windy 500 (AKA:… READ MORE
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2018 Windy 500 wrap-up
509 miles this year makes it 4,083 total Windy 500 miles ridden for me so far. That’s the equivalent of… READ MORE
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Windy 500 2017 wrap-up
Yeah, that just happened. The Windy 500 just became the most spectacular thing ever. And you weren’t there. It was… READ MORE
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2016 Windy 500 wrap-up
AKA: 14.5 Reasons Riding Bikes 500 Miles Will Make You More Awesome The 2016 Windy 500 rolled out sort of on-time… READ MORE
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2015 Windy 500… you had to be there.
Alright folks, here it is – the one and only Windy 500 has once again shocked and amazed. Old friends… READ MORE
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2015 Windy 500, Day 5
It’s officially over. Until next year. Could not have been better. Look for the official Ride Report in the next… READ MORE
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The Windy 500 hits the big time
We’re proud to introduce our first 2015 in-kind sponsor: Pabst Blue Ribbon! I was pretty stoked when this Windy… READ MORE
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2015 Windy 500 dates announced!
I flew to Switzerland last night to attend the official press announcement for the 2015 Windy 500. The event was a… READ MORE
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2014 Windy 500 is in the books
Technology 1. Duwayne 0. What turned out to the be the best Windy 500 ever fell short in only one… READ MORE
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Windy 500 v4.0: It’s the Final Countdown
We are nowhere near as cool or sexy as these long-maned Swedish man-whores, but we’re not opposed to letting a… READ MORE
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2014 Windy 500 Info Session
2014 is here, time to plan for the annual Windy 500: (Head North, pedal, sleep, turn around, pedal. Done!) Interested?… READ MORE
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2014 Windy 500
North, to the U.P. August 1 – 4, 2014 4 days, 500 miles, 2 states. Rain is guaranteed. Questions? jasonkayzar@gmail.com READ MORE
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2013 Windy 500 report
Here we go… Mile 0. The kinder, gentler version of the Windy rolled out on July 25th and ended up… READ MORE
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2013 Windy 500 Update
First off – I am personally guaranteeing that we’ll have much warmer weather than this morning’s ride for the 2013 Windy… READ MORE
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9 Reasons Not To Miss The 2013 Windy 500
164 days until the 2013 edition of the Windy 500 rolls… This year, we’ve added a new twist: those in… READ MORE
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2013 Windy 500 route
The 2013 Recipe for the Windy 500 is almost fully baked: It’s a bit of Urban mixed with a bit… READ MORE
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2012 Windy 500 is in the books!
Where do I start?? Here is the complete list of rules for the event: You must ride a bike 500+… READ MORE
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2nd Annual “Windy 500” rolls in 1 week…
4 days, 500 miles, 2 states and more flat tires then most people have in a lifetime! www.windy500.com Flat tires… READ MORE
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WINDY 500 planning meeting (with beer) on February 2nd!
Note: February 2nd is the correct date for the planning meeting. I originally posted the wrong date (Feb 7). The… READ MORE
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2012 Windy 500 dates are set!
Next year’s 2nd Windy 500 will take place from August 3rd to August 6th. 500 miles in 4 days. Nothing… READ MORE
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2011 “Windy 500” ride report
Q: “Where are you guys from? A: “Milwaukee” Q: “Where you headed?” A: (depended on what day it was) “Shawano”… READ MORE
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Words to ride by
“I love to travel, but hate to arrive.”
~ Albert Einstein
…Faster than Last
About
Bikes, brothers, and the annual Ride of Stupidity. Fifteen years of the Windy 500 and counting.
...Faster than Last 