Lisa and I brought our Ritchey Breakaways during a recent convention trip to Chicago just so we could get around and see more of the town easily. Maybe go on a casual weekend lycra ride Saturday or Sunday during our trip extension. A few hours along the Lake shore would have been dandy. Fifty miles tops. I made no advanced plans for any of this, nor had any idea of the city layout, nor the possibilities for any extended ride prior to our departure. Heck, we'd already spent three nights in Chicago and still didn't have much of a clue -- other than the most obvious choice along the lake shore -- of where to go for a ride. Up to this point, I had been doing all my roaming and exploring on foot.

Cut to Friday night, in our room at the W Hotel on Adams Street, laptop aglow with Google Maps on the desk: half a dozen other browser tabs are open to various city landmark reference sites, and neighborhood references. In a moment, I'm inspired and have an idea. Not just for a Saturday ride, but for a ramble around a 100 square mile area of Chicago's neighborhoods too the following day. Weather had been pretty good all week, and looked promising for both days of the weekend.

Chicago-Kenosha Route Map

"Hey, Lisa, lookit." I sputter. "We're only 50 miles or so from the Wisconsin border. If we ride to Kenosha and back, it could be 200K. Wanna do that tomorrow?"

"Sure! Lets" says Lisa without a moment's hesitation, apparently forgetting as much as I that she's still recovering from a lingering flu.

And so the destination was set. 200K, ya no big whup. Sure. Far cry from a casual fifty miler though. Carefree adventure travels with us every where we go, apparently, and certainly having our own bikes along on trips makes extemporaneous riding like this not completely unreasonable. Basically, we made up our own urban brevet overnight: I'll dub it the CKC 200K.


Without a map, guide or route sheet to depend on, I had to take a general mental snapshot of the area map along the Western shore of Lake Michigan between the center of Chicago and the state border. A published book by David Johnsen talks about Sheridan Road as the hallmark route in this part of Illinois. This would be the foundation of our route out to Wisconsin, and I'd decided it would be generally an out-and-back to minimize risks of getting lost on the return.

Getting to Sheridan Rd. from our hotel was a quick exercise of riding across Grant Park, then north as far as the Lakefront multi-use trail goes. On any given Summer day, this trail gets pretty busy with runners and casual cyclists. Today, there also happened to be a benefit marathon going on. Weaving through all the foot and fat tire traffic wasn't too bad, but definitely required some patience.

We emerged onto Sheridan Rd. itself for the first time at the northern terminus of Lakeshore Drive, in Evanston and the area of Loyola University. From here, getting to Kenosha is theoretically simple: stay on Sheridan the whole way up. But Sheridan Rd. has got to be the most indirect road I've ever seen, with many turns, street name changes and confusing disconnects along the way. It helped a lot to find numerous signs that labeled the road in tandem with signs for the official Lake Michigan Circle Tour. Still, those circle tour signs are more intended for motorists and directed traffic to some undesirably busy parts of Sheridan Rd. Basically, I had to rely on navigational instincts to take a lot of side street detours to avoid these sections, and circumnavigate numerous road construction closures.

The upshot of the sidestreet wiggle between Wilmette and Zion was coincidental avoidance of high traffic on Sheridan. It's a busy and shoulderless two-lane road most of the way, and some sections do require vigilance and courage while exposed closely to brisk moving traffic. At the same time, we serendipitously discovered some hidden neighborhood gems along the way, like small lakefront neighborhood parks, historic sites, and... cobblestone roads!! Yeeaaa!!!

Cobblestones aside, the pavement on most of Sheridan Rd. outside of the wealthier residential neighborhoods pretty much sucks. For as battered as Illinois gets by winter every year, this is to be expected. So on one hand I was pretty happy I had my bike set up with really fat (35mm) cyclocross tires to soak up the bumps and holes, but the distance of our ride also had me envying Lisa's 25mm road tires. This was definitely the longest ride I've done with any sort of knobby fat tire.

Interestingly, two extended sections of Sheridan Rd. are completely and explicitly prohibited to bicycle access, which I thought was kind'a shitty. In the village of Glencoe, cyclists are required to take a parallel route on Green Bay Road instead, bypassing a curvy and slightly hilly section of Sheridan close to the lake water. Bummer, I thought. This probably would have been the hilliest part of an otherwise 100% pancake flat ride. The other prohibited section was within the city limits of Lake Bluff, which requires riders to take a parallel bike path.


Sheridan Road shows dramatically different faces and character numerous times between Chicago and Kenosha. In a way, this ride was probably one of the best possible ways to get a macro sense of communities living and working in this region. Loyola, Northwestern's Evanston campus, and Lake Forest each had very different collegiate neighborhood environments. Wilmette, Winnetka, Glencoe, Highland Park, and Lake Forest were collectively a smorgasbord tour of beautiful stately homes representing a dizzying array of architecture disciplines. Tudor, Colonial, Gothic Revival, Spanish and Mission, Modern, Plantation, Victorian, Craftsman and Prairie; and noticeably few contemporary post-modern homes.

In line with this region's evident architectural significance (analogous to Chicago's riverfront commercial architecture legacy), the area boasts one of the highest concentrations of residences designed by Frank Lloyd Wright, two of which are easily identifiable and right on Sheridan Road, including the Ward A. Willits home. One other in the village of Glencoe, built in 1905 and a bit more obscured, was built by Wright for -- as it happens -- a bicycle manufacturer, William A. Glasner. According to the Glencoe Historic Preservation Commission, Glasner awarded Wright as the winner of a contest to design a "servant-free" home for two, which cost $5,000.

North of Lake Forest, Sheridan Road takes on a much different face in lower working class communities. Towns like Lake Bluff, Waukegan and Zion are populated mostly by people who probably work in a number of manufacturing facilities, the most conspicuous of which is the foul smelling Abbott Laboratories. Somewhere in the area of the Great Lakes Naval Training Center, signage for Sheridan Rd., the Circle Tour and the Lake Bluff bike path all but disappeared, and Lisa and I found ourselves wandering into a pretty tough section of town in North Chicago (a city in itself 35 miles due north of the city of Chicago). The appearance and vibe there strongly resembled gang territories in Richmond, Oakland and East Palo Alto back in Northern California. We stopped at a gas station in the center of town to refill our water bottles, but agreed this probably wasn't the sort of place for nonchalant exploration and it would be most prudent to retrace our steps to Sheridan Road.


I've read and heard many things that suggest the city of Chicago has made concerted efforts to be more bicycle friendly in the vein of accomplishments by cities like Portland, Oregon. Does it measure up? As of today, sort of. And since Chicago's now officially an official 2016 Summer Olympics host city candidate, I can only imagine it will get better in time.

I think it's a pretty good bike town. Striped dedicated bike lanes are pretty scarce, but there's a well-signed city bike route network, and of course riding paths along the shores of Lake Michigan. Our bikes were the key to covering a lot of ground in Chi town, discovering dozens of neighborhoods over a 100-square mile area from parts of the South Side, to Hyde Park, to Humboldt Park, West Town, Pilsen and the West Loop, Soldier Field and the museum campus. Drivers seem to be very tolerant here and not once were we ever buzzed or honked at while on city streets. Generally, city traffic here seems to move at a more civil pace than in most other cities I've visited anyway.

There's fewer aggro road antics, but for some reason, more erratic behavior that was difficult to read compared to situations I encounter in NYC and other big cities. A certain kind of suddenness and illogical manner of directional change by all sorts -- drivers, pedestrians AND cyclists -- threw me off pretty frequently in this town. I feel confident in my ability to foresee situations and read mixed traffic pretty well, but Chicago was a weird different story. I can't explain why so many times people would choose to knowingly travel in my path when their original line of travel was free and clear to begin with.

Chicago has some of the strictest visible rules I've seen prohibiting cycling on sidewalks. I suppose this is partly the reason why motorists are generally more accepting of bikes on the roadway. The ordinance is a bit confusing in some parts of the city though, namely Millennium Park and the adjacent parts of Michigan Ave, and areas around Navy Pier where bike trails spill directly and seamlessly onto wide sidewalks.

Oddly, the cycling scene and vibe in Chicago seems kind'a insular. Riders on the streets tend to be in their own world and aren't very fraternal. This applies all the more in the northern suburbs where NO club/weekend cyclist appears to care about smiling, or exchanging gestures to even say hi or 'sup, or even acknowledging your presence. Fine by me, but I really wonder why cyclists here have major sticks up the ass when every other Chicagoan is dizzy with summertime free-spirited joy.


Finally, a juicy middle finger salute to the unreasonably restrictive rule-mongers at the Swissôtel with a level of snobbery that was so out of line, and out of character for the hopelessly mediocre property that it is.

We were staying there for three nights only because it was the host of Lisa's convention. On our second day in town, we took the bikes out and explored the city for a couple of hours. Upon our return, the doorman was visibly surprised to see us making strides to enter the hotel.

"You can't take those into the hotel" he says. I looked at him in disbelief, mutter "That's ridiculous", shook my head like we just heard a lousy joke, and we went our merry way.

Twenty paces later, nearing the elevators, two earbud wearing members of security rush our way and halted us. At this point, I'm wearing my best WTF expression as I hear the recital of the hotel policy that states we cannot bring our bikes into our fairly spacious room. A third security person emerges. Wow, this is getting serious.

Lisa and I backed up and parked ourselves by the concierge desk and tried to reason with security, saying this is the first time we've ever had to deal with a policy in any hotel anywhere, of every service quality level and every price scale. I request the presence of the manager so I can reason with her/him. Meanwhile, we were detained at the concierge desk across the guest check-in area under watch of security for 20 minutes, like we stole something.

The manager and one of the security staff were having a private téte-a-téte in plain view of me, and I had to invite myself to the conversation. Talk to ME, Mr. Douchenozzle manager. "Sir," he says, "our hotel policy..." bla bla bla bla bla. Same shit, different mouth.

I inquire where then we're expected to store the bikes. He suggests the garage. "No. Unnacceptable." I quickly answered. Do they really care to deal with the liability of bike theft over whatever it is they're so afraid might happen if we bring our bikes into the room?

"The other thing we would normally do is have our bell hop store your bicycles for you in a luggage room." Problem: the bell hop's whispering in your ear that the luggage room is under construction and unavailable.

I patiently explained to Douchenozzle manager, as I previously had to security personnel, twice, that our bikes were of a design that allowed them to come apart and be stored inside suitcases. After that, it's as if no bicycle is even in the room. Just some luggage.

"Sir... we have to keep your bikes in the garage, we can't have you store them in the room."

"No." I appeared even more incredulous. Maybe even unsettled at this point. "Look, let's please be reasonable. Your storage room is unavailable, your garage is a high risk area for these bikes to be stolen. If you really insist on having us keep our bikes in the garage, I'd like a $5,000 deposit on each bike."

Then Douchenozzel manager gave me the WTF look. Naturally, and just the sort of reaction I expected and wanted. I was just waiting for him to insist that even if I were to put said break-apart bikes back into their suitcase-like cases, I'd have to do that work on the garage floor.

"The reason for our policy is that because we've had these bike marathons and guests have just destroyed our rooms."

INCROYABLE!! Really??? Sacre bleu!! Savage cyclists at the Swissôtel. Imagine that.

"So you're suggesting that I'm an untrustworthy and disrespectful guest, is that it?" I'm reduced to assuring the slave manager that I've been a guest at some nice hotels, some $1000 a night places, and none have taken issue with me having a bike in the room. "Really, I'm a courteous and respectful guest." I was tempted to say I've had a better reception at a Best Western than he was giving me, but I held back.

"I'm not saying that you're not, sir...." he desperately spewed.

"That's certainly not the feeling I get right now." I retorted.

A sigh. Then, "How long are you staying with us, sir?"

Two more nights, I informed.

Another sigh. "OK, only since our storage room is unavailable, we'll let you bring the bikes upstairs."

I wasn't in the mood to keep up this engaging conversation, so I just as quickly nodded, said "Very well. Thank you." and we marched to the elevator.

Minutes later, in the room, feeling only partially vindicated, the phone rang. "Sir, this is Andrew, the manager. We just spoke downstairs. We've decided, we really can't allow you to store the bicycles in the room. But we'll let you keep them there tonight. Tomorrow, they'll have to be stored in the garage."

With the most intense amount of restraint I've had to exercise in many moons, I simply said "OK" and hung up. Enough. I decided to break at least Lisa's bike apart, and store it in the case so if the hotel were ever indignant enough to check up on us, I could plainly show we had a bag in the room, not a bike.

In my record-time dissassembly of Lisa's bike, I remembered, too, that the check-in manager told me the day before that they were the only Swissôtel in the U.S. I could have sworn I'd seen them in New York and Boston before. Then suddenly I got it: With this quality of service, they're simply headed toward extinction. Of course.

But this incident left me paranoid thinking perhaps all hotels in Chicago would be like this. Would the W hotel we were moving to after the conference have the same policy? Lisa checked by phone, pretending to be a guest without a reservation yet. The hotel attendant there said "Your bikes come apart and fit inside a suitcase?? That's cool!"

OK, we were encouraged, but still a little leery when we got there. Sure enough though, we put the W hotel's friendliness to the test, arriving from our long ride all grubby and having to wade -- with bikes -- through a river of very well dressed yuppy party goers in the lobby. Not one hotel employee batted an eyelash. And the concierge next to the elevators smiled and wished us a good evening.

Distance: 124 miles | Elevation gain: not noteworthy | Ride time: 9h30m
Info: Johnsen, David. Biking Illinois (general reference only)
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