509 miles this year makes it 4,083 total Windy 500 miles ridden for me so far. That’s the equivalent of a round-trip ride from Toronto, Canada to the Gulf of Mexico and back. For the rest of you Pop Tarts, your total Windy mileage ranges somewhere between 4,083 (McArdle) & 509 (everyone else). What matters most though is not the mileage, it’s the adventure.
This year, as with every year, the ride rolled from my house. Day 1 is a mix of veterans and newbies, well-wishers and tag-alongs who roll to the first stop with us and then head home. It usually takes a few hours after we roll out to find our rhythm. Some are better than others at riding 2 up in big groups. Those who’ve raced are comfortable on someone’s wheel at 30 mph, riding shoulder to shoulder. That type of confidence makes for very smooth, safe, confident riding. Others, not so much. This group is a mixed bag of experience and ability, so for some, it’s a bit of a crash course in technique (without the actual crash part). Eventually, people figure it out, and we do our best to ride as one unit for the next 3 1/2 days.
Day 1, stop 1, ALMA’S Cafe in Allenton. They’ve treated us way too well over the years, and after 35-40 miles of riding on fumes, their breakfast sandwiches are better than peanut butter dipped in peanut butter.
Our favorite stop is always Kwik Trip, because… it’s Kwik Trip:
Eventually, the hills find us:
We ride all day, and nights are dinners and renewing friendships.
Mornings are van loading and slowly rolling out of whatever parking lot we have taken over.
It’s riding, chatting, working, recovering and most of all, making memories that will last a lifetime:
As always, if you weren’t there, you’ll never know.
The Windy 500 is just a bike ride, but it changes you, makes you better. The hardest day for me is always Day 5. The day when I wake up and shower and put on people clothes and drive to work and sit down at my desk. And I don’t pedal. Not once. And I don’t climb. And I don’t descend, screaming into a valley, tucked into my handlebars at 54, 55, 56 mph, with 5 guys right next to me, all doing the same, all smiling, ear to ear. I just sit.
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It has taken me quite a while to sit down and compose my thoughts about this year’s ride. The Windy 500 has become an extremely important part of my life, and I generally start planning the next ride when we roll into my driveway on Day 4. During the ride, we discuss ways to improve the experience, and I arrive home with scraps of hotel paper and bar napkins with random thoughts and ideas scribbled down on them. This year, I rolled into my driveway alone. And it was over. I showered up and sat down to a home-cooked meal with my wife and kids. The rest of the group rolled on to Wauwatosa to celebrate Bill Finn’s birthday. I had developed some kind of sinus cold on Day 2 and once I cleaned up I was done for the day. And I didn’t think about next year’s ride until a few days later.
For 4 days on the ride, I control what I do. I control my time, my efforts, my thoughts. Well, maybe not my thoughts. But I really don’t think about manipulating Excel spreadsheets much. Or my mortgage. Or yard work. I just think about riding. And talking to my close friends. Mostly about nothing. Locker room talk and juvenile jokes. But sometimes it’s about really important stuff. Really deep stuff. The kind of stuff you can talk about when there’s nothing to do all day but move your legs in hundreds of thousands of circles.
That’s my Windy 500. I work really hard at times, not so hard at other times. I wake up, grab some coffee and wait for the hotel’s breakfast to fire up. Then I get ready and I ride. All day. For 4 days. It’s as pure as it gets.
But this was Year 8, and I’ve done this before. 7 times before. And it was an adventure. A long time ago. In fact, I heard some of the guys who weren’t there in those early years telling the stories, and they even got some of it right.
Every year, somewhere along the route, people will ask:
“What are you riding for?”
I was recently reminded of this by my friend Dr. Long, and it stuck in my head like glue. The Windy 500 has become an event without a purpose. Without a True North. Why indeed?
Do you know what homogenized milk is, Billy? It’s bland Billy. Bland. And the Windy is pretty well homogenized. We eat in fancy restaurants and we have name tags, Billy. Name tags!
Don’t know how to change a tire Jimmy? It’s OK, we bring lots of extra wheels! 
And at the end of your long day, you get to swim and relax with other busy execs!
Meh. I think it’s time to shake it up again.
Don’t get me wrong – this ride is still SUPER awesome. The route, the riders, the endless miles in the saddle. But it’s become so big, such an event, that it’s not what it was originally intended to be. For me.
For many of the other guys that did the ride this year, and for those who have done it in past years, maybe it’s exactly what they want it to be. But the ride is at an intersection, and for Year 9, 2019, I need more. Or maybe less.
Here’s the complete list of rules for the original Windy 500, back from 2011:
- You must ride a bike 500+ miles in 4 days
- You must ride in at least 2 states
Unfortunately, the rules have been amended over the years to include:
- Hotels must have pools. And hot tubs.
- Support vehicle must be stocked with refreshments, spare wheels, spare bikes, (maybe spare riders next year?)
- Rest stops can take as long as the anyone wants them to.
- Anyone can make up rules as we go…
I realize that this is not just my ride anymore. Heck, I’m barely even responsible for it now. And don’t get me wrong, I like the pools. I look forward to cooling down after the ride. But the sense of adventure that launched this journey is long gone. So 2019’s route will have 2 fully supported options:
Group 1:
Faster guys, stronger climbers, fewer stops. NOT race pace, but it will be challenging.
Group 2:
Casual pace. Riders will re-group at the tops of climbs. More frequent rest stops. This group will most likely leave 1/2 hour prior to Group 1. Both Groups will meet at the lunch stop and at the hotel. No need for the faster guys to feel held back and no need for the more casual guys to turn themselves inside out. And having 2 smaller groups will do wonders for safety.
That’s all. We’ll probably go West again. The route is really beautiful and certainly challenging. And everyone is welcome back.
Oh, and to answer the question “What are you riding for?” I defer to McArdle’s answer:
“AWESOMENESS.”
...Faster than Last 