Alright folks, here it is – the one and only Windy 500 has once again shocked and amazed. Old friends got reacquainted, new friends were made, beers were consumed and miles were ridden. If you weren’t there, here’s a little glimpse of what you missed. If you WERE there, consider yourself down, and take a minute to sop it up…
Roll out – Friday, July 31, late (as usual)…

Out on the open road, and within about 1/2 a mile we lost our sag. We went right and the van went left. (Note from Al Krueger – 10 miles later, Jason’s bike that he cobbled together the night before, unsurprisingly and finally, gave out. So, we sat on the side of the road for 35 minutes in the lovely Holy Hill area while we waited to get re-grouped with the sag, get his bike that actually worked and then we continued on.) 10 miles later we re-grouped and continued on. The winds whipped up, making it impossible to communicate but we hammered on. Eventually we fell into a rhythm, but not before stopping to all yell at each other a little. The 5th Windy 500 was off to a very predictable start.

Further up the road (Oshkosh) we made the first of many mandatory stops for Mexican food and hydration.


Back on the road, and back to the brutal head and crosswinds. This year the Windy finally lived up to its name. The was very little shelter from the wind, but having 21 riders sharing the work certainly helped a ton.

Friday evening I was treated to a fantastic birthday celebration. It’s easy to have fun when you “know SO many people…”


A great time was had by all, or so I’ve heard. Back on the road on Saturday, a spectacular day all around.

It wasn’t long before we checked off one of the few Windy requirements: cross a state line.

The best part of rolling into the U.P. has become a stop at the legendary La Cabaña.



After a relatively long but uneventful day in the saddle, we finally reached our turn-around.

And then there was Sunday. A very long day on tap, 152 miles, and the forecast looked absolutely beautiful… a week ago. By that morning the forecasters were predicting severe thunderstorms, hail and we even heard 60 mph winds at one point.

The weather started off OK, but shortly into the ride there was a millisecond of lost focus and a couple of guys went down hard. Road rash, bruised parts and egos, and a completely shredded derailleur hangar on Jeremy’s bike. Then, to add insult to injury, the first storm hit. Al made quick work of repairing the bike damage, and we found a temporary haven with the Briguglios in their Lake house.

While Al was hard at work fixing bikes in a musty shed, the rest of us got to work screwing around.


Just as we’d fall into a groove, the storms would whip up out of nowhere. A quick stop for fuel at a gas station would turn into shelter from the hail and driving wind and rain within 5 minutes.


Although this day was the second longest in Windy history, and definitely the worst weather ever, it was epic. Everyone will remember it, and it made for some awesome riding.


Sunday evening we enjoyed pizzas by the pool and hot tub, along with Jameson and “guess my age” with strangers. I’m not sure who won, but Finn definitely lost. Monday morning we cashed in the points we earned on Sunday and were treated to the best weather we could have asked for.






502 miles – done. Definitely one for the books. At this point, it’s hard to have a favorite year. What’s not hard to do, is start thinking about next year’s trip already.
This year’s ride is dedicated to Sugs who lost a week-long battle for his life after a serious accident last week. They don’t make many like him, and the world will miss you Rob. WORS, the Rampage, and countless other places and events where friends gather to ride bikes together will never be the same.
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