First I’d like to thank Lindsay for suggesting this location, the Bloomingdale Trail was something I hadn’t discovered yet. It’s essentially an elevated train line that is no longer in service. It runs from 3500 W. Bloomindale up to about 1700 W. Bloomingdale and it’s full of graffiti, grit and broken glass. In fact, if you haven’t been I guarantee that you’ve seen the trail because you’ve most definitely passed beneath one of its many viaducts that run across the city.
The land used to be owned by the Canadian Pacific Railway but it is now the focus of several local groups with the intent on building a 2 mile long, narrow, elevated multi use public park. The idea has been approved by the city and Rahm Emanuel has made it a goal of his to ensure this unique park is built. The trail offers incredibly unique views of the Chicago skyline as well as some very intimate moments with Bucktown residents as it passes very close to living rooms and kitchens at several points.
I would highly recommend getting down there to see it in its current state before it is turned into a beautifully manicured public park. Technically speaking, there is no trespassing but hundreds of people a day are seen walking and jogging along the trail so I assume the cops won’t bug you. The entrance point I used was in the NE corner of Milwaukee and Bloomingdale but I know that there are several other entrances. Thanks again Lindsay for the suggestion.