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Sailing in the Windy City

Posted by on Aug 16, 02:38 PM
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From Madison there is a bicycle trail built on a retired railroad grade that runs strait to the lake and Milwaukee. On a pleasantly bright and warm day Randall and I Trail Ridedeparted in search of this 70 mile route across the state of Wisconsin. After our usual 2+ hour preparation (lubing the chains, airing up the tires and a fuel stop at the grocer) we were of and pedaling the bumpy roads. It took at least an hour to find the trail head, but boy was it worth it! Our route was lined with a dense wall of deciduous treas on either side and was a pancake-flat, smooth jaunt all the way. Riding through quaint little towns, through serene wheat fields, and over bridges that crossed whispering slews and lazy, brown rivers this trail bumped Wisconsin’s marks to A+ for bicycle touring in my grade book. A fantastically tasty ice cream cone toward the end of the ride really hit the spot!

Crestfallen, I mused about what lodgings we might find in a large city at midnight.

BasilicaIn Milwaukee we spun through the strait and wide streets after dusk in search of an unsecured WIFI signal so that I could retrieve the phone number of our potential host. We finally parked in a residential area not far from the ‘bad’ part of town and found a signal. To my Welcome to Illinoisdisappointment Randall and I had had a miscommunication and our potential host was the same that had sent me a message saying that that night would not work. Crestfallen, I mused about what lodgings we might find in a large city at midnight. Indeed, none of our options could Sa!lingbe described as savory and inviting. Then, we were approached by some inquisitive locals just arriving home from a what must have been a festive evening. After the usual Q and A session
Sailing ViewRandall asked if we might camp in there yard that night. The guy generously obliged us and we rolled our long-haul rigs into the back yard, which was landscaped tastefully and was graced Relaxed...with a (cool) hot tub and a pond. The former we were invited to use at will. Goal!

Ira and AndreaThe next day’s ride was equally fine. After a visit to the famous and astonishingly beautiful basilica, built entirely by the generosity of poor Polish immigrants about one hundred years ago, Chicagowe clipped south on the lakeside drives in the warm sun until we stopped for a break with some frozen yogurt and snacks at a peaceful little park to take a breather. Many curious individuals approached us and kindly wished us good luck with the expedition after some playful conversation. The manager of the bike shop a few blocks away was Cycling through the cityvery amped about the trip and helped us out with some small necessities. This days ride would wind us all the way into Illinois. Just after the state line we had to stop at the Harbor Lights Restaurant for the Friday evening fish fry. Words simply cannot describe the delight it brings to Lakeside traildevour a delicately breaded fillet of tilapia alongside a helping of garlic-roasted potatoes at the conclusion of a long day of touring. That night we camped in a nature preserve that we shared with countless blood-sucking mosquitoes.

MeSaturday’s trip would see us in Chicago at the end of the day. It was a nice, hot day and we continued along the lake shore through some fabulously upscale resort towns and a not-so-fabulous post-industrial ghost towns. Thank goodness for the bicycle trails that shelter vĂ©lophiles and runners from the suburban traffic north of Chicago. In Evanston Randall and I became separated and I decided to go for a solo sail in a Hobey Cat in the ideal weather on this hot and breezy Midwest afternoon. As soon as I had left A nice evening viewshore the wind picked up. I bobbled around trying to get the boat to point in the right direction. It was embarrassing. But, I finally succeeded and pulled my first tack after two tries. My second took eleven tries. Finally, I figured out how to manipulate the jib (front sail) to pull the front around the wind, and it was smooth sailing. The wind became so strong that it was quite easy with my little ballast to lift the outside hull out of the water at top speed, but I have to admit it was a little scary!

Whizzing through busy traffic and dodging side-view mirrors on your bicycle is a great way to get your thrills in the Windy City, but you must first achieve a heightened sense of awareness if you plan to survive.

City ShotRandall and I met up again in the late afternoon at our host’s house in the Ukrainian Village of Chicago. Rows of lovely brick apartments lined the shady streets and the ubiquitous city aromas of ethnic foods and garbage wafted through the balmy afternoon air. Our hosts were a couple, recently-married, named Ira and Andrea, and the welcome-to-our-place beer was more than welcome. We barbecued shish kebabs and sipped fine scotch for the evening and finally retired, completely spent. PowerThe next day was windy and fine and we loaded up on food and relaxation. My good friend, Carl, from Bellingham dropped by and we all went for a mouthwatering Chicago pizza that evening. Whizzing through busy traffic and dodging side-view mirrors on your bicycle is a great way to get your thrills in the Windy City, but you must first achieve a heightened sense of awareness if you plan to survive. Ira (along with most urban vĂ©lophiles in the city) rides a fixed-gear bike. This type only has one gear and no freewheel so you cannot coast. Brakes are unnecessary since you can slow down by resisting the forward pedal stroke. It’s mechanically simple but it takes practice to ride!

For a more intimate view of Chicago check out Ira’s blog. Monday was spent tying up loose ends and eating Chicago-style hot dogs (Yum.). We got a late start on our ride and around 5 o’clock bid adieu to our good hosts and pedaled the beautiful lakeside bike path out of the city.

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Last Updated: Jun 26, 11:50 AM

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  • Calories Burnt: 2,301,650
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