The Midwest Tour Continues

Stage 2: Chicago to Madison

This is the second installment of this story. Click Here to read the first part.

It’s the summer of 2013, and I’m sitting at my desk in my home office with a black Uni-Ball Vision Elite in my right hand, furiously scribbling ideas for my impending trip to the midwest. I was planning day three, and I had a problem: Dave Carter, our intended interview for the day, wasn’t going to be available until the following Monday. It meant that we had one day to kill, and since I didn’t have another Members Only profile lined up, I wasn’t sure what exactly to do. As I flipped between Google Maps and my notebook, a flash of inspiration hit me.

Wrigley Field. Now that was a place where I could kill an afternoon.

Sunday Funday

It was day three, and both Carl and I had just left Pontiac, Ill. to head towards the windy city. We were on a tight deadline: I had made plans for the early afternoon, and Carl was set to wander across the city with his camera in tow to take some shots. We wanted to spend as much time in town as possible to soak in the city and everything it has to offer, but we also wanted to have some space to ourselves to a certain extent. Chicago was going to be a solid break for two people who were out on the road together for an extended period.

We checked in at our hotel, the Wyndham Blake Chicago, right off Dearborn and Congress. Parking was just like in St. Louis, which is to say it was virtually non-existent. There were garages nearby and a valet, but not a lot of options for someone riding their Gold Wing — at least not ones that didn’t require a walk of some kind. But once we got inside, we forgot all about parking and checked out the hotel and our rooms. Holy cow were they awesome!

Each room was mammoth for a one bedroom, and they both had flat-screen TVs, huge showers and accompanying bathrooms. Carl and I had our own rooms, but truthfully, it wouldn’t have been a stretch to put two people in the same one because everything was gigantic. The beds were the best ones we slept on for the entire trip, and this was, by far, the nicest place we stayed. But the best part of all of it was the price. As GWRRA Members, we had a discounted rate through Wyndham hotels, and the price saved us a good amount of money, particularly when compared to other spots in town. Impressive.

But I didn’t have much time to enjoy the room before I had to get going. While Carl took his camera and shot as much of downtown as he could, I was on my way to legendary Wrigley Field to watch the Chicago Cubs play the Atlanta Braves. Before the trip, I ordered a ticket from and for a few bucks I was sitting just behind home plate, 10 rows back. To get there, I had to hop on the subway and take the red line north, something I wasn’t too thrilled to do.

Even though I grew up outside of Boston, I’m still very much a suburban guy at heart. I couldn’t remember the last time I had been on a subway, and I was genuinely concerned that something bad would happen. Paranoid? Wussy? Sure, all of the above. But just in case, I made sure to keep my wits about me and my money in my front pockets.

As I boarded the red line, I found a seat and parked myself there for the duration of the trip. Our hotel was about 25 minutes away from Wrigley by subway, so we had quite a distance to travel. As we bumped down the rails, more and more Cubs fans boarded until the entire car was a swirl of blues and reds. When we hit Addison, I disembarked and followed the masses to the field. All my concerns about public safety washed away as I saw Wrigley Field in front of me. I was pumped.

I’m a die-hard Boston Red Sox guy, but as a fan of the sport, you’ve got to appreciate the Cubbies. Wrigley field is the second oldest stadium in the MLB (second to Boston’s Fenway Park), and only by a year. The history of the team, what with their not winning a World Series for 100+ years, is something I can relate to as a Red Sox fan. But even if I didn’t like baseball, Wrigley Field is still one of those places that you have to add to your bucket list. The history alone is amazing.

I won’t get into the nuances of the game or bore you with details (the Cubs lost), but I will say that come the third inning I found myself freezing and shivering uncontrollably. For most Chicago natives, it was probably just a normal day with a slight breeze. But I was losing feeling in my toes, so I purchased a hooded sweatshirt from the team shop. Shortly before the game officially ended, I called up Carl and found a spot that we could meet between the two of us. I hopped back on the subway, headed south, and we met in the middle on North Michigan Avenue.

What I didn’t know at the time was that we had stumbled into the Magnificent Mile, a stretch of North Michigan Ave that has some of the best shopping in the country. Carl wanted to go to the Apple store to buy a new laptop (boy, that’s a long story), and I just wanted to see the city. So after meeting up at the subway, we wandered to the Apple Store, checked it out for a bit, then pointed ourselves south towards our hotel. Even though my knee was bothering me, I pushed us to walk the two miles or so back, and I’m glad I did.

North Michigan Ave is a beautiful place to walk, and the people watching alone is worth it. When we hit the Michigan Avenue bridge, we took a moment to shoot the boats going down the Chicago River and sightsee a bit. Many different movies have been shot right in that area, but what struck me was the scenes I remembered from The Dark Knight. Once we crossed the river, we grabbed a late snack/early dinner at a local restaurant, then walked the rest of the way to the hotel. We both adjourned to our respective rooms and collapsed for the night. It was a good day.

Madison or Bust (But First, a Stop)

Carl and I hit the road at 6am so that we could be in Crystal Lake, Ill. by 10 or so, plus make a stop for breakfast on the way. We were sure that four hours would be enough time to make it there, grab some food and have our interview with Dave. We were about as close to wrong as it gets.

It took us two hours to get out of Chicago. Two. Long. Hours. The delay caused us to skip our first scheduled adventure of the day, and instead get to our meeting spot with Dave Carter a bit earlier than expected. Because of that, we decided to grab breakfast at a restaurant in Algonquin, Ill. named Burnt Toast.

With about 45 minutes to kill, we sat down for a relaxing meal. Between the two of us, there were quite a few breakfast staples including pancakes, bacon, eggs, coffee, and, of course, toast (although it wasn’t burnt). The food was amazing, service spectacular and we found ourself with enough time to catch up on emails and the like using the free Wi-Fi. Relatively fast Wi-Fi is a precious commodity nowadays, and we certainly appreciated it.

After our meeting with Dave and his wife, Gwen, at the nearby Colonial Cafe, we did our photoshoot down right next to the Fox River, right off the 62. When that was complete we said our goodbyes and headed off north towards Madison.

The trip to Madison was uneventful, as we mostly took side roads to get there. We took the 31 north towards the 12, then took that towards Kettle Moraine Forest, which you can read about later in this issue. With the sun setting on our day, we pointed the rental car west to Madison, Wisc., ready to collapse in our comfortable rooms.

Destination: West

We were almost done with our midwest tour, but we still had three stops to go, one of them which was completely unplanned. See, while we were in St. Louis on day two, Bob Phelps asked us about the path we were taking for the trip. We’re pointing out destinations and he brings up a particular tourist spot. “Have you been there?” he asks excitedly. “You have to go there. It’s a must see. Do it, you won’t regret it.”

Where was that hotspot and was it worth the trip? Guess we’ll find out in our final installment of the midwest tour, in our March issue, along with a few other surprises. See you then.

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