I'm wondering if anyone could offer some suggestions for routes around the city for some interesting urban exploration.  I'd like to get out and ride around taking pictures of anything interesting.  Perhaps some interesting architecture/infrastructure, or something with historical significance.  All suggestions welcome!     

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Not sure how active they are, but there is an "Urban Explorers" Group on this site.
I saw that. It doesn't seem like that group really got going. I'm also not really looking to break into places to catch some asbestos poisoning :) , just find interesting spots around town that are off the beaten path so to speak.
Ravenswood Avenue is one of my favorite rides--there's some old industrial architecture there and some pretty gardens too.
This may sound odd or morbid, but I enjoy riding through Rosehill Cemetery; which is easily accessible from Ravenswood Avenue as there is an entrance off of there. Some famous people are interred there as well as some really interesting monuments, statues, and some really pretty ponds and such. It's a nice quiet ride. Just watch out for the gate closing times, as you can get locked in there if you're not careful.
This may be obvious, but if not, check out the Boulevard System for some great historic architecture and Park District treasures. Garfield Park Conservatory is not to be missed.

http://www.logansquarepreservation.org/boulevardhistory.html

http://www.garfield-conservatory.org/
They allow bikes there? The one time I tried to ride through Graceland I was promptly told bikes weren't allowed. Cars are though. Go figure.

Melanie said:
This may sound odd or morbid, but I enjoy riding through Rosehill Cemetery; which is easily accessible from Ravenswood Avenue as there is an entrance off of there. Some famous people are interred there as well as some really interesting monuments, statues, and some really pretty ponds and such. It's a nice quiet ride. Just watch out for the gate closing times, as you can get locked in there if you're not careful.
I don't think it is allowed, but no one has ever said for me to leave or anything, and I go through daily on my commute, go right past the offices, the caretakers and everything, and I have not been stopped once. I see other people on bikes in there, too. I think Graceland is just in a different neighborhood, so maybe they are really strict about it.
Check out the North Shore Channel Trail that follows the river north from Lawrence. You can start at Addison heading north on California -> Manor Ave and pick up the trail at Lawrence.

http://www.yelp.com/biz/north-channel-trail-chicago
Nope. I was kicked out once.

They told us we were welcome but not our bikes; they were 'obtrusive.'


Jared said:
They allow bikes there? The one time I tried to ride through Graceland I was promptly told bikes weren't allowed. Cars are though. Go figure.

Melanie said:
This may sound odd or morbid, but I enjoy riding through Rosehill Cemetery; which is easily accessible from Ravenswood Avenue as there is an entrance off of there. Some famous people are interred there as well as some really interesting monuments, statues, and some really pretty ponds and such. It's a nice quiet ride. Just watch out for the gate closing times, as you can get locked in there if you're not careful.
just off of roosevelt, (DeKoven St). the chicago fire academy is there, this is where the chicago fire started.

Oz Park near lincoln park high school
Alta Vista Terrace (near wrigley field) very interesting architecture.
South Shore Country Club
Personally I like the near west side industrial areas to tool around. Some good urban scenery for picture taking, not a lot of traffic. Curbs and other assorted stuff to jump in case you're into that.
Their signs say no bikes, but I've never been stopped. If you're interested, try entering at Western/Bryn Mawr(?). Less presence. This and Graceland are two of my favorite spots when the fall colors are out.

And I'd second Alta Vista Terrace and the neighborhoods just north of there off of Sheridan.

notoriousDUG said:
Nope. I was kicked out once.

They told us we were welcome but not our bikes; they were 'obtrusive.'


Jared said:
They allow bikes there? The one time I tried to ride through Graceland I was promptly told bikes weren't allowed. Cars are though. Go figure.

Melanie said:
This may sound odd or morbid, but I enjoy riding through Rosehill Cemetery; which is easily accessible from Ravenswood Avenue as there is an entrance off of there. Some famous people are interred there as well as some really interesting monuments, statues, and some really pretty ponds and such. It's a nice quiet ride. Just watch out for the gate closing times, as you can get locked in there if you're not careful.

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