An outsider’s Chicago bike itineraries


Photo by Alan Scott Walker

This guest post was submitted by Tim Eyre, who crosses the country frequently for his job as a manager with Extra Space Storage. Eyre is a cycling enthusiast and he’s found that exploring the cities he visits via bicycle is a good way to connect with and learn about the communities he visits. He offers the following bike route suggestions for visitors to Chicago, but locals may find them interesting as well.

Chicagoans, don’t take what you have for granted. My weekdays are spent on the road, and it’s sheer grace that I discovered bicycling to keep me sane a few years back. Wherever I’m working, I can always find an escape by cruising the town on two-wheels. As any cyclist knows, the disconnect between the observer and the community that car travel creates quickly fades away when you’re self-propelled and out in the open air. Neighborhoods come alive, and we actually meet other people.

Of all the cities I regularly ride in, Chicago may be the best. The 18.5-mile Lakefront Trail is obviously the heart of this city’s bike scene, and understandably chock-full of locals and visitors like myself taking in the view. Recently, however, I’ve been branching out, taking advantage of the city’s interactive bike map, a tool that urbanites in other metropolises across the globe would drool over. If you’ve never checked it out, it details roads with existing bike lanes, shared lanes, and recommended routes.

With a little pre-planning and my GPS-equipped phone in my pocket, I’ve been discovering new favorite rides across Chicago, from Bucktown to Little Italy. Whether you’ve got an hour after work or a full day to explore, here’s my outsider’s suggestions for a perfect ride.

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Isaac Grigsby of WIG Bags


Photo by John; all others courtesy of WIG Bags

This is the second in a series of interviews looking into what it will take for Chicago to develop a thriving bike-related business community, focusing on messenger bags. Earlier I talked to Tia Meilinger from New York City’s Vaya Bags to learn how she launched a successful global business. Last week I caught up with Isaac Grigsby from Chicago’s WIG Bags over breakfast at the West River Café, 4400 N. Kedzie in Albany Park, a few blocks from his workshop, to discuss his business and his views on the local scene.

In the early 2000s Grigsby started WIG, Wheels in Gyration – “It means the wheels are always turning, I’m always trying to figure something out or put something together,” he says. Since then he’s made thousands of custom bags and shipped them to every corner of the globe. But he says he has no interest in having his products – messenger bags, backpacks, camera bags and more – sitting on store shelves.

We talked about the origins of his business, the features of his courier bags, how he gets the word out about his products and why he doesn’t like sewing custom images on the flaps of his bags. Grigsby also gave his opinion about why it’s difficult to launch a bike business in this city and told me what it’s like sewing carrying cases for rocket-propelled grenade launchers. Continue reading Isaac Grigsby of WIG Bags