I’m deep into training for this year’s Tour des Trees to benefit TREE Fund, our annual 500+ mile cycling event that raises funds and friends for the organization I lead. Marcia was attending a conference yesterday, so with a full, sunny, solo day at my disposal, I decided to get my first century ride (100+ miles) of the season done. Generally, when I want a longer ride in Chicago, I head south from our home near the Loop, and I try to stay away from the densely crowded Lake Shore trails, the “Hipster Highway” Milwaukee Avenue corridor, and/or various trail systems north of us that are popular with young couples pushing mega-strollers or pulling unpredictable little dogs along on their strings. I can log a lot of miles quickly with far fewer unplanned or unexpected stops when I ride into areas that are less apt to attract hordes of bike share tourists wobbling around taking selfies as they roll.

Of course, my approach to distance training means I log a lot of time and a lot of miles in South Chicago, which many (most?) of my Loop or North Chicago dwelling neighbors  are apt to immediately declare unsafe and unsound, given crime rates and other demographic factors there. (This same concern applies to and is voiced about West Chicago, which I also ride through if I am heading out toward my office in Naperville). That reaction frankly bothers me, a lot, and I really don’t want to be “that guy” who judges huge swaths of his home city as fundamentally bad without ever entering said parts of the city. I’m not stupid, obviously, and I understand risk calculation and have a good sense of self-awareness and self-preservation, so I keep alert to my surroundings, I don’t go into spaces or places where I could be easily isolated, and if my radar gives me a sense of “unsafe,” I move expeditiously onward, and I adapt my route the next time I’m in that neighborhood to avoid the area that made me uncomfortable. But I do that in the Loop and in Streeterville or River North too, or wherever I am. Common sense rules apply, always.

So at any rate, off I rolled yesterday, and as I have done before, I left the Lake Shore trail systems and cut west on Roosevelt north of Museum Campus and then headed south on Halsted, a quick-moving north-south arterial with good bike lanes in both directions. It was a quiet Sunday morning without much traffic, so I was able to get into and mostly through a good chunk of South Chicago pretty quickly. The map at the top of this article shows (most of) my ride for the day. Eagle eyed observers will note, though, that the green start marker (where I live) and the red finish marker (where I ended this route) are not the same place, and therein lies the heart of the day’s story.

Around mile 28, as I was heading back north and east after riding the Major Taylor Trail out to Whistler Woods and beyond, I hit a sharp pavement cut near the intersection of Vincennes and 103rd with my weigh squarely on my rear bike wheel, which immediately popped (likely a spoke pinch) and went flat. No worries, though, I am a well-prepared cyclist and I had both a spare tube and a patch kit with me, since I know that flats happen when you do a lot of city riding on rough pavement. I pulled over under a nice street tree in a grassy area across the street from Holy Zion Missionary Baptist Church, changed my tire, hydrated a bit, and rolled on.

I really like riding and exploring the weird industrial areas around the far southeast of Chicago, and on into northwestern Indiana. There are some gorgeous bodies of water, lots of parks, fishing, pleasant outdoors vistas abounding, though they are often located cheek-to-jowl with factories, or heavy loading facilities, or landfills, or huge high-speed highway systems. I spent a good chunk of the day yesterday in that area, then headed back up along the shoreline toward home. I purposefully rolled into and along the beaches of Calumet Park, Rainbow Beach Park, and the South Shore Nature Sanctuary, and it was just great to bask in the beautiful day there and people watch, as there were tons of folks out enjoying the weather. Calumet Park’s visitors were mostly Hispanic, Rainbow Beach’s were mostly black, and I liked being there with them all, and didn’t feel the least bit out of place as I cruised through and said “howdy” to other riders or folks on the trail, all of whom were just as friendly to me.

Around mile 80, I was pushing north on the Lake Shore Trail, and an annoying chilly headwind off the Lake was blowing in my face, so I decided to cut back across the city to Halsted again, and then take that back north toward home, doing whatever zig-zags I needed to do to push my mileage total over 100. I cut through Hyde Park and Washington Park, and cruised on West 51st under the large conglomeration of rail tracks west of the Dan Ryan Expressway. Just before I emerged into daylight again, though, I hit a pile of glass that was hidden in the shadows, and my back tire went flat again.

More of an annoyance this time than the first time, since it meant I had to patch, rather than just replacing, the tube. So I rolled up close to the intersection of Halsted and 51st, popped off the back tire, pulled the tube out and pumped it up, and heard/saw several punctures, larger than a simple patch would handle, never mind the slivers of glass that I could feel inside the actual tire, without needle-nose pliers to tweeze them out.

So phooey, there I was at Mile 86, and I figured the riding day was done. I turned off my bike computer, saved my ride (hence the different stop/start points in the map), went into the Citgo Station on the corner of 51st and Halsted, got some chips and a soda, chit-chatted with the folks hanging outside of the station, and called to get a cab home that could handle my bike.

All good. No worries. Everything’s still social and sociable, I’m still feeling fine about the multi-culti glory of Chicago and meeting folks where they are, as they are.

The cab dispatcher took my name and location and said she would post the pickup, and that a driver would call my cell phone when they accepted the fare. Still no problems; there was a bus shelter on the corner so I sat down in the shade and waited for my phone to ring. Which it didn’t. So I called the dispatcher again after 20 minutes or so, and she said she was on it, and a driver would call me soon, honest.

As I write this article 24 hours later, I still have not received that call from a driver.

Soooooo . . . cabs don’t readily go deep into the South Side. I guess I knew that. But, hey, I’m a regular Chicago CTA commuter, never afraid to get on a bus, so I decided I’d just catch the Number 8 line up Halsted to somewhere in the West Loop where cabs would be more common, then snag a ride home. I looked at my phone at 3:45 and it told me a bus going my way should be there at my stop at 3:48. Perfect!

Except . . . not. There was no sign of a bus until about 4:10, when I saw one rolling up from the South. I got up so I could quickly get my bike into the transporter rack, except the bus just rolled right past me: “Not in Service” the message board above the driver said.

Hmmm. That’s weird. Was there a service disruption? Weekend hours? Broken bus?  I figured I’d wait for the next scheduled one (30 minutes later) and see what happened.

A few minutes later, though, a large black car pulled up in front of me and the driver rolled down his window. “Oh, cool, the cab’s here,” I thought.

But then the driver stuck his out and said “Are you okay?”

“Yeah, I’m fine,” I said. “I’ve got a flat bike tire, and I can’t get a cab, so I’m just waiting to catch a bus.”

“I think I should give you a lift out of here right now,” the driver said. “This is not a place where you should be standing for very long. I’m not sure if anyone would target you exactly, but I can tell you that bad things happen on this corner. It’s not a good place for you to stand and wait. Will you accept my ride?”

I realized by this point that I was speaking to an under-cover or off-duty Chicago Police Officer. Since I was planning to meet Marcia for an evening reception and had something of a hard time deadline, I accepted the Officer’s invite in the interest of moving on, tossed my bike in the trunk of his unmarked patrol car, and rolled north with him. He was considerate and somewhat apologetic as we chatted, noting that I looked so obviously out of place in that bus shelter that he knew something was awry, and also noting that he has responded to numerous “incidents” at that corner over the years. Since he presumed I wasn’t choosing to be there, he thought he should offer to help me move on. That’s all. No biggie. Glad to be of service.

He gave me a lift as far as the Halsted Orange Line Stop, where I could catch the El train into the Loop. I thanked him, sincerely, and pushed my bike toward the train station — upon the door of which was a big sign saying “Due to high volume Chicago Pride Day traffic, bikes are not permitted on our trains today. We apologize for any inconvenience.”

Goddammit!

Okay, next plan: I know that cyclists are friendly, helpful folks, as a breed. Whenever I see a bike on the side of the road, I always call out to see if the rider needs help, or a tool, or whatever. It’s just what you do. So I walked back to Halsted and turned North, clacking and clattering along in my bike cleats, hoping some cyclist might take pity upon me as I walked next to the bike lane.

Within five minutes, one did: a guy named Ray, who told me there was a bike shop south on Halsted (behind me now) that was open until 5:00, and that he had just come from there. It was about 4:40 now, so I thanked him and said I didn’t think I could make it there in time and that I’d just keep schlepping on toward home. So he rolled north away from me — but then rolled back a couple of minutes later and said a Southbound bus was coming, and he would ride up and tell it to hold at its next stop for a minute if I could quickly walk my bike up there to meet it.

And Ray did that. And the bus driver waited for me. And I told the bus driver where I was going and he actually made an interim stop so I could get into Blue City Cycles with about five minutes to spare before closing time. And they pulled the glass bits out of my tire, got me a new tube, and had me rolling again within about ten minutes.

I had to start a new ride on my bike computer, though, since I’d closed the old one out. I logged six more miles, bringing my total biked for the day to 92, having lost at least eight miles of measurable road time to bus and squad car rides. Dangit dangit dangit!! That’s like planning a marathon and quitting at mile 25. Doesn’t have the same bragging rights appeal or self-satisfaction elements, at all. Grrr.

Oh well. When it was done, I had a lovely evening with Marcia (it was our 29th wedding anniversary yesterday, which we had celebrated the night before at the sublime Topolombampo) and saw some good friends from Albany who were in town for the conference Marcia was attending. But as I went to bed last night and rode my bus and train to work this morning, I found myself reflecting on four takeaway points about my Denied Century Day:

1. It reminds me how nice and important it is that the Tour des Trees is a supported event; the riding days go quicker when you have friends on the road with you, and our Tour Director, Paul Wood of Black Bear Adventures has a great team behind him, so that in the case of a small incident like mine, or God forbid a bigger one, support is never far away on the route, with multiple vehicles and multiple teams ready to respond to riders when needed, never mind the great snack and lunch stops along the way.

2. It really hammered home for me one of the great social inequity issues in our City in terms of how difficult it is for folks in the South Side to depend on public transit or use cabs to get around, with the corollary factor that this makes it even harder for them to get good jobs outside of their immediate neighborhoods, no matter how much they want them, or how hard they work to secure them. We so take for granted our ubiquitous cabs, buses, trains and other instantly available forms of transit in the “nice” parts of the city. Not everyone in Chicago is that fortunate, though, and that’s both a shame and a structural failure of planning, economics and imagination, in terms of serving all of the city’s citizens, no matter where they live. We all deserve that, right?

3. The day made me more committed, not less, to riding smartly in the South Side. People were good to me. They were kind and pleasant. Nice things happened. I was not afraid. I had some enjoyable conversations and saw some interesting community sites, as I almost always do. I understand and appreciate the police officer stopping to check on me, though I know some folks might take umbrage with his actions or even my acceptance of his ride offer. But I think that our exchange was less indicative of any nefarious underlying racism, and more indicative of the fact that if other riders from “my” part of the city weren’t afraid of riding where I ride, then I wouldn’t have looked so obviously out of place to an officer who works that neighborhood on a daily basis. I hope that some day the area around the Citgo station on 52st and Halsted features more folks who look like me, or look different in different ways, on bikes, on foot, in cabs, whatever. We’ve got all sorts here in Chicago. The more we regularly interact comfortably together in all of our neighborhoods, the better off we’ll all be.

4. And finally, okay, I will carry multiple bike tubes with me from now on. In decades of riding, I’ve never needed more than one (plus the patch kit) in a single riding day, but now that those odds have finally broken against me, I’ll suck it up and add another one to my kit each day before I ride.

So, all in all, a good day with a good ending and some good lessons learned and some good things to think about.

But, dammmmmmmmnnnn . . . . 92 miles!!! CENTURY DENIED!!!! So close, and yet, no credit, son. Pack it up and try again. Do not pass go. Game over. You lose.

Oh well. I will likely ride three century days on the Tour des Trees itself this year, so if I don’t get any in before then, I’ll have no shortage of them once we make it to Ohio!