I’m long long looooong overdue on this post — we went on Mother’s Day and here it is nearly Father’s Day. My little project suffered terrible neglect in the last month.
Recollection
We toyed with buying a condo in Woodlawn when we were first relocating. Selling the townhouse we owned in Wisconsin was an arduous process, though (this was 2007-2008) and after the place had been on the market a few months, we nixed the idea of trying to buy here in the city. We’ve been happily renting since.
And other than that, I’m not sure I’ve been back here.
Rambling
I took the Jackson Park Express (route 6) down to the Midway Plaisance, the northern border of the neighborhood. I hadn’t been the express since I left Hyde Park. I was early getting there and wandered around UC a bit before heading to Backstory Cafe.

As you appoach Backstory Cafe
I met up with S. at Backstory mid-morning for a bite to eat. I met S. at the Mac ‘n’ Cheese Mingler I went to back in March. She’s a writer, from Chicago, and recently back in the city — she blogs here.
Anyway, the cafe is aptly named, tucked away, easy to miss at the edge of the UC campus on a backstreet behind a construction site. It doesn’t look like much as you approach, but it’s bright and sunny, warm, and staff are cheerful and helpful. Great coffee and cheap brunch — in sum, a cozy spot to begin from.
From here we headed to Jackson Park. And we saw quite a bit of it — the Wooded Island, Osaka Gardens, soccer fields, the big gold Lady. It was a gorgeous day.


Poor S. wasn’t prepared for the epic wandering. I enjoy my rambles, but they can be *very* tiring, particularly when you’re not expecting them.
We discovered a golf course at the end of the park — or I did. knew it was there, but I was delighted to discover that you can golf in the city limits. Even though I don’t golf. I just like surprises.
S. knew the golf course — and in fact was a veritable fountain of knowledge about the neighborhood, game and enthusiastic … fantastic company.
The day was beautiful — I really could not get enough of being outside in the park, despite the geese following us around and the lack of paths and signs at the south end (I got a bit turned around). But no matter.

When we had our fill and S.’s feet were thoroughly beaten up, we headed back toward the cafe & her car where we parted ways (S., we walked over 5 miles!) and headed down 63rd Street toward the Green Line. Walking west, the neighborhood gradually gives way from very new single family homes to apartment buildings, empty lots and low-end retail. Though I have to say, for the number of empty lots you pass as you near the Green line, it really feels well-kept. Less littered. It’s a much more comfortable feeling place than East Garfield Park was. At least on this particular day with the sun shining and several miles of walking on my legs.
* * *
Woodlawn is what I’m really starting to think of as a truly Chicago neighborhood — there isn’t one thing that characterizes it: it’s a mishmash of upper class, middle class, working class, largely, but not entirely black in racial makeup, spread out in the spanse between a golf course and a dollar store, an active community, friendly … I love those neighborhoods.
The whole set of pictures
Rundown
Population (2000 Census) 27,086
94.6% Black or African American
3.0% White
1.1% Hispanic or Latino
1.1% Two or more races
0.8% Asian
0.3% Some other race
0.2% American Indian and Alaska Native
0.0% Native Hawaiian and Other Pacific Islander
Median household income $21,482
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Wards
5th, 6th, 20th
Neighborhoods within
Woodlawn, West Woodlawn, Parkway Gardens
Landmarks
Statue of the Republic, Midway Plaisance, Jackson Park, Osaka Gardens
Transportation
The terminus for one arm of the Green line is 63rd Street at Cottage Grove, in the west end of the neighborhood. Lake Shore Drive and Metra service the neighborhood on the east side.
History
The Encyclopedia of Chicago History’s summary |
Useful Links
City of Chicago’s map of the area (.pdf file)
Woodlawn on Wikipedia
on The Chicago Tribune
on EveryBlock
on WikiTravel
Woodlawn photos from neighborhoods.chicago.il.us
Know what I should visit when I come to your neighborhood?
Email me at pirateblogs[at]gmail[dot]com or leave a comment. Or if I missed something on a past visit, I want to know!