Day 1

Friday, August 31, 2012
Chicago – Milwaukee
93 Miles

Ride Data

The night before I left I couldn’t sleep at all.  I was all packed and ready to go with a trunk full of spare parts and gear for Heather to bring with her to Milwaukee that night.  For the first three days she was planning on meeting me at the end of each day.  This was a plus because I didn’t need to carry extra nutrition and supplies for the upcoming days.  I cleaned the bike from head to toe, greased and oiled all moving parts and attached my rack, lights, and bottles.  I packed my nutrition for the next day, charged the Garmin and got my Arkel Trunk Bag packed.  When I lay down in bed that night it dawned on me that I wouldn’t see my own bed again for a long time.  But the excitement of what it would be like to actually get on the road for 10 days was overwhelming.  After months of planning and years of dreaming about it, the trip was finally here!



Picture of me walking out the door (Taken by my neighbor Dan)

Friday, I woke up very early and couldn’t get back to sleep.  Heather left for work and I was left to do the final preparations alone before setting off.  I ate an egg sandwich and changed into my bike gear which would be my only change of clothes for the next 10 days.  It took about an hour to finally get everything packed and situated for the day.  But as I was heading out the door I realized there was no one to take an inaugural photo…   It felt wrong to start this 1,000 mile journey without a “before” photo, so I rang the neighbors doorbell.  Just as I thought no one would answer he came to the door in his robe.  Dan is super nice and I asked him if he would take my picture.  He gave me a weird look but of course said “no problem” standing in the yard he took a quick picture as I explained what I was doing.  He looked at me as if I had two heads but said “good luck and be safe!!” with that I was off.

The bike by my favorite spot just north of Highland Park

The weather that morning was absolutely beautiful!  Light wind, sunny and around 70 degrees.  It was exactly 9:00 AM.  As I rode down the street and around the first corner I couldn’t help but wonder what I was getting myself into and what the next 10 days would be like.  The one thing I remember from those first few miles is that I couldn’t stop smiling.  It seems funny now looking back but I just couldn’t wipe that darn smile off my face.  I headed north on my normal route up to Highland Park then beyond to the Wisconsin border.  I stopped at the border to take a picture of the Wisconsin sign, which had the iconic Circle Tour sign, that I was so used to seeing.  Only three more states to go!  The first 50 miles were the easiest I’ve ever ridden.  I felt great, the legs felt great, and the weather was cool.  At mile 50 I made a poignant, left turn which was one of the scariest turns I’d ever taken.  It was the turning point for all my century rides up to this point.  Up until now I would ride north for 50 miles then turn around and come home to complete my century rides.  This was the furthest north I’d ever been.  As I turned left I said to myself “here we go… uncharted territory”  Everything was no unfamiliar and new to me and the real adventure was about to begin. 



Crossing into Wisconsin

After 60 miles the day started to heat up and things got serious.  I hit long stretches of gravel trail which ran directly under power lines so there was absolutely no shade at all. The midday heat radiated off the stone and I cooked like an egg in a frying pan.  It was about this time that the wind picked up out of the north and became a powerful headwind.  Going into mile 70 the heat was intense and so was the wind.  The terrain got much hillier and the riding got a lot harder.  I also hit some bad sections of trail and road which required me to slow down.  A few times I even got lost jumping from trails to roads and had to search for the route.  I decided that it was probably better to stick to actual roads rather than try to switch between trails and roads.  I came across this same scenario many more times as the days unfolded.  As I entered South Milwaukee I caught my first glimpse of the city.   I had dreamed for years about riding up to Milwaukee and now I was finally doing it.  It was an amazing feeling, and once again I found myself smiling like a fool.

Unbelievably long stretch under the power lines.  Temp 90+ Degrees

First view of Milwaukee

 The last 15 miles of the day were a breeze and I started feeling good again and as I entered the city. It was exciting to see the change of scenery and be close to completing the first day.  I cruised up the Milwaukee lakefront trail and through a large park.  It was full of people and had many trails crisscrossing their way through the trees.  The scenery of the lake and tress were beautiful and there was a soft breeze cooling me down from the heat of the day.  I passed a museum with a really cool cantilever bridge going over the road and stopped to take a few pictures.  I road past the park and into downtown and then up a giant hill making my way to the hotel.  I got lost a couple times turning from roads onto trails but was able to get back onto the right trail and cruised into the hotel.  The hotel was right on the river which sounded better on paper than it actually was.  The trickle of a river was nothing special to look at and when I arrived at around 3:00 pm there wasn’t much activity at all.  The first thing I did was take my shoes off.  My feet felt like they were on fire and were very sore.  I checked in and walked in my stocking feet up to the room.  After changing quickly I went down to search out some food.

Downtown Milwaukee

Cool pedestrian bridge in Milwaukee

View of a fountain in the park overlooking lake in Milwaukee

After going into the restaurant and finding no one working I introduced myself to the nearest family and asked where everyone was… they gave me kind of a weird look but said there was a waitress around.  Finally she came up and I took a seat at the bar.  For some reason she came around the bar and took my order while standing next to me which I thought was a little weird.  After getting a cold root beer and a sandwich I was chowing away when I looked down and realized my fly was standing wide open…. AND since I was packing light I was going “commando”…. Oh My!!! I zipped up and shook my head.  Now it all made sense.



The bike in my hotel room at the end of Day 1

Finally, when I was I went back up to my room to read.  The one luxury item I took (only on day 1) was my book.  I was reading Stephen King the Dark Tower series and was very close to the end of a book.  It was getting so good I couldn’t put it down.  SO I hauled the 1,000 page novel up to Milwaukee in my bike bag so I could read it before Heather got there for the evening.  It was hilarious to see that I’d cut the edges of the maps out so as not to carry the extra weight then carried a 2 lb. novel.  But it was worth it and I spent the rest of the afternoon napping and reading.


That night Heather arrived and we went out to the Cheesecake Factory for dinner.  It was one of the only times I ate everything on my plate.  I was beyond hungry and drank two huge glasses of chocolate milk.  After returning home for the night we realized I’d left my extra big 32 oz. water bottle at the restaurant.  Realizing my hydration and water was everything on this trip I had no choice but to get out of bed and go back out and to the restaurant and get it.  Collapsing into bed exhausted I happily, reflected back… Day 1 was in the books.