
Every great story needs a demon; an anti-hero. In 2011, ours showed up in full force: flat tires, wrong turns, racing the setting sun with no lights, aching legs, no Plan B, and the kind of grit that only emerges when everything goes sideways. That was the very first Windy 500, it was chaos wrapped in camaraderie, and it set the tone for what became an annual pilgrimage of pain, perseverance, and pedal strokes.
But here’s the paradox: over the years, the better we got, the less the ride fought back.
This year, the demon didn’t even bother to show up. The weather (sort of) cooperated. The bikes held up. The legs were strong. Logistics ran like clockwork. And while that’s a testament to how far we’ve come, it also left me staring at a blank computer screen wondering how to tell this story for the 15th time.
For me, adversity isn’t just the path, it’s the fuel. It’s my “why”. It’s what transforms effort into meaning, and chaos into legend. I’ve spent the vast majority of my life fighting my own invisible demons, and the Windy turned that inside to outside every year. I would roll out of my driveway inhaling clean, fresh air and exhaling pain and struggle. The harder I would force myself to work, the lighter I would become. So what happens when the obstacles disappear? When the path is smooth, and the rhetorical winds, for once, are at our backs?
This year’s Windy 500 wasn’t about conquering hardship. It was about what remains when hardship fades: the people, the rituals, the quiet satisfaction of doing what we love, with the people we love. It is no longer a battle, now just a celebration. And maybe that’s the story worth telling.
The Stats
Under the category of “…spirit of adventure…” we’ve experimented with many different things to keep the ride fresh and interesting over the years:
Headcount – year one was 4 dudes, no SAG, no room for error. Subsequent years topped 25 riders (I never remember the specifics). Coordinating a ride for that many people was a rolling circus, it’s way too many. Science has now proven that 12 is about the perfect number.
Routes – the original 3 rules were: Ride 500 miles, in 4 days, and cross a state line. We’ve since broken all 3 of them. We’ve tried a 5 day trip (too long). We’ve tried an urban trip (an absolute disaster – WI to IL to IN and back), and we’ve done over 500 and less than 500 miles. Once we ran out of directions to go to cross a state line, we starting repeating routes. That was fine the first time, but not the 3rd. We’ve since shit-canned the notion of leaving WI unless it serves the route on that particular year. The biggest reason for that change is the fact that we now rent a “home base” on night #1, and stay there for the entire trip. We used to rent 3 separate hotels on our way to and from a destination. Having the base camp means that our Saturday & Sunday routes are “out and backs”. Now, we’d rather stay somewhere interesting that has a ton of riding options, than race to a generic destination just because it’s 250 miles from my front door.
Terrain – we’ve done pancake flat routes to the UP (boring) and dick-punch hilly routes (multiple trips to Winona , MN, which were fun for some and Hell on Earth for others). The best routes are somewhere in the middle: endless miles of sloping rollers.
Accommodations – We’ve stayed in shitbag hotels and Hyatts, and now multiple VRBOs. The VRBOs rule (as long as we have enough beds…) because we live like a big family on vacation instead of pairs of dudes staying in individual rooms every night. Plus, we can cook our own meals.
And for those keeping track, here’s our updated stats list:
Disclaimer – I use my computer for these stats. Computers may vary by model, especially for total elevation gain. Mine is likely short of actual, but oh well.)
Total miles traveled: 7,463. Yes, I know. 500 x15=7,500. Year 1 we logged 535 miles, and we continued to bank rollover miles through 2021. Since 2022 though the Windy 500 has been the “Windy 4 mumble mumble…”, and now we’re in a deficit. There have been a few requests to dial it back up to 500+ in 2026. I’m down.
Total elevation gained: 186,642 feet or 35.35 miles. That’s a lot. Unless you see this stat: Total elevation gain in the 2025 Tour de France was 172,240 feet. We’ve had flat route years – 2015 was only 5,825 total feet of climbing, and we’ve tried more challenging routes – 2018 was 18,731 feet of elevation. Several riders clocked 20,000+ ft on their computers on this year’s ride, which would make it the tallest ever. However, mine only said 17,037, making it (officially) the 4th hilliest on record.
Total ride time: 435 hours, 6 minutes, or roughly 18 days and 8 hours. That’s an overall average speed of 17.15. This is the stat I’ve struggled with the most, for absolutely no reason. This is, has always been, and will always be an “adventure ride”. A “fun ride”. It is not a race, or race training, or a big dick contest, but I’ve always had a hard time just slowing down and fully enjoying the ride. In 2011 (year 1) we did 545 miles at 18.8 mph. Only 4 guys, no SAG. 3 of us doing the vast majority of the work after halfway through Day 1, which ended up being the longest in Windy history: 163 miles. That means that other years, our average was below 17 mph. I find it really hard to enjoy riding that slow, when we are doing 4 back-to-back centuries in a row. A few weeks ago, I went out for a 13 mile ride with my wife and we averaged 13 mph. We had a blast, but that pace for a day of the Windy would have meant 10 hours of riding, plus rest stops, or about 13-14 hours total. Starting at 8am and finishing at 10pm? No thanks. While I always seem to be the dickhead pushing the pace for no reason, this year I was definitely more relaxed. I hope to continue that trend next year.
Top speed: 55.5 mph. Again, for me anyway, fast = fun. Some years we climb a lot, which means we get to descend a lot. Some people (me!) love bombing the downhills at max speed, others love to just coast down and enjoy the scenery. Either way, we always regroup at the bottom.
Ok, on to 2025…
One thing we’ve never been able to outrun is the distance limitation of leaving from my driveway every year. Regardless of which direction we go, we can only get 250 miles away before we have to turn around. But this year, Chris and bc hatched a plan to overcome that barrier. Enter MF Fred!
Fred is our retired SAG driver. We randomly stopped to change a flat in his driveway one year, we met him, we hung out, and the next year he was our driver. That’s the kind of stuff that happens on the Windy. He and his amazing wife live in Beaver Dam, about 60 miles NW of my house. This year, we all drove to Fred’s and took off from his driveway, giving us a 60 mile extension cord to utilize. The results? Success! Plus, we got a badass lead-out from his lovely wife on her trike.
Aside from that, our age and experience has finally begun to rule out the stuff we don’t want or don’t like or don’t need to do. We’ve really whittled it down to the purest form we can: ride all day, hang out together at night, get up and do it again.
Repeat that process every August until we die…

After that? Nothing but riding bikes and being awesome…












“Riding out” the storm that brought historic flooding to Wisconsin…










16th edition: July 31 – August 2, 2026…























































































































































































































































































As always, if you weren’t there, you’ll never know.









































































































































