Day 0 + 1
Riding the bike for the first time
Day 1: Chicago, IL to Joliet - 41.1 miles, 371 feet elevation gain
I flew out on a redeye which was subsequently delayed by nearly two hours. I tried to sleep on the plane, knowing I had a big day- ha! more like a big three week adventure - ahead of me, but it was moot. Crammed into Basic Economy seating and landing at 7:30am, the only thing you can do is question why you are traveling in the first place.
Why am I riding my bike 1,200+ miles in rain, wind, hail — over hundreds of miles of pavement, gravel, highway? To answer that question, is to understand two things about me: 1) I HATE bicycling. 2) I HATE being bad at something. I dont really know if I hate biking because I’m bad at it, though it sure feels like it. In order to “try” and like it, I’m giving it the ol’Daphne Feng spin by dreaming wildly and making it into an excessively arduous and kinda pointless journey(?), you know, an adventure!
Initially, I dreamed this ride up in 2009. It makes sense because at that point I’d really only biked about 8 times in my adult life. I had wimpy legs and wanted to accelerate some ‘saddle time’ as the kids say, to the point where I was comfortable and strong on the bike. So, I shipped my bike to Chicago where I was attending an event. I had 25 days to ride my bike somewhere. Why not Route 66? At 2,500 miles, I’d have to average 100 miles a day with no rest days. It being my first cycle tour, I decided to pivoted and instead rode my bike 1,100 miles from Chicago back to New York City. Every since then, I have dreamed of actualizing that little dream to ride Route 66 and “get good at biking.”
Fast forward ten years and its 2019. I’m staring down the barrel of midlife and wondering what I can do to sprinkle some excitement into my life. I am reminded that Route 66 is still an untamed goal so I jump at the chance to put plans in place. Never mind that I haven’t ridden nor have I owned a bike in the past six years. Never mind that I have a week to put all the logistics of this trip in place, buy a bike, and summon the fitness to brave 1,200 miles. These concerns were like road rash on the way to glory. Once I decided I was going to do it, I quickly began a quest to try as many bikes in the Bay Area to see what type would be suitable. Then I called bike shops in Chicago to see what could be available before booking my ticket.
After I disembarked in Chicago from my cramped redeye, I grabbed breakfast with an old college bestie before heading to Village Cycle Center to get my bike “STORMY”, nee Trek Emonda SL 6, when they opened. I brought some gear with me but soon discovered that it was not compatible with the bike. I spent another few hours going to a number of bike shops to replace what I had brought. Finally, after one trip to Fedex to send back the unused gear, I was ready to clip into my clipless LOOK pedals and go for my first ride on the bike. Four miles later, at Buckingham Fountain, I officially kicked off my Route 66 adventure. There was one area when I was few miles to my lodging, a casino, where there was a fallen tree, but otherwise, it was a flat, easy spin to Joliet.
Wish me luck!
