I cheated a bit and took the Yellow Line to Dempster.
|The original North Shore station house for Dempster.|
This is kind of an odd station. There's no reason to get off here, other than to pick up your parked car or transfer to a bus line. There used to be rows of commercial buildings either way, but nothing one would consider a destination. Even if you were travelling to Old Orchard Shopping Center, it would probably be easier to take the bus from Howard.
The original station is actually across the parking lot. It's a beautiful 1920s building that references the local bungalow and prairie styles. Since Starbucks moved in, it's also one of the better bathroom stops.
To the west is the Edens Expressway. No matter what street you take going west, you are going to run into the problem of crossing this monstrosity. When it was built in the 1950s, no one seems to have imagined that it would be necessary to cross it by foot. I recommend using the south side of Dempster; it's just easier to deal with the exit ramps than with all the maniacs trying to get on.
|How most people spend their days.|
After that, it's a nice bike ride up the sidewalk through Morton Grove. The scenery mainly consists of mid-century strip malls that have been converted over the years to modern CVS' and Walgreens' and such.
|Remodeled a bit, but still a recognizable 60s gas station|
You'll want to switch to the north side of Dempster before getting to Milwaukee. I recommend doing so at Harrer Park, where you can also visit Morton Grove's Historical Museum.
It's an old German farmhouse that was built in 1888 and eventually moved from the old mill road which is now Lincoln Avenue (and a history trip for another day.) They're never open when I go by, but have been assured that the house is full of historical stuff to look at.
|Plus, they have a large artillery gun in case Skokie ever tries to attack.|
Now that we are past the area served by the old commuter train lines, little ranch houses and corner drug stores are giving way to weird, mid-century housing developments. You can see how the two interstate highways changed everything out here. If you couldn't afford a boxy house in Morton Grove, you could always drive to a "starter" townhouse further out from the city.
|Washington Avenue, in Niles|
Which brings us to the crossing at Milwaukee Avenue. There is an insane underpass that makes it fairly impossible to cross Dempster here. If you get stuck on the south side of the street and try to cross Milwaukee, there is no sidewalk waiting for you. So, unless you have mad Frogger skills, you want to already be on the north side of the street.
Once you make it, you can visit the Niles Historical Museum. This used to be the 1920s Cook County Sheriff's headquarters, so it's not as impressive from the outside as Morton Grove's museum. But, I have been inside, and they do have neat historical stuff to look at. Just remember to bring some cash and leave a donation.
I'll take a break for now and pick up tomorrow with more sub-divisions, strip malls and weird highway monuments.