South Lakefront Trail
Obviously this site springs from a love of Chicago Parks and a drive to explore. In wandering about the city, I sometimes think about playground tours - visiting multiple playgrounds in one outing - and this has created a lingering question:
How many playgrounds can you visit without crossing a road?
There are many examples of two playgrounds on one site or within easy walking distance - but what's the longest tour you can take without crossing a road, street, driveway, boulevard, or other car-centric pathway?
Exploring the south lakefront gives one answer to these question.
63rd Street Beach Playground
Start at 63rd Street Beach with a unique playground literally on the beach and steps from Lake Michigan. Then head north on the lakefront trail.
[Aside: if you wanted to risk two street crossings, you could exist the lakefront trail at the 57th Street underpass and go to Dickerson Playground and Chrysalis Playground pretty easily. But I'm sticking to the rules as I defined them and won't count these.]
Shore Playground in Burnham Park
If you take the 55th Street underpass you can get to Shore Playground. After this stop, get back on the lakefront trail and keep heading north.
Washington (Harold) Park - Playground
Exiting via the 51st Street overpass and backtracking by the Chicago Park systems' only model yacht basin will provide access to Harold Washington Park.
[You pass quite close by the 47th Street Playground in Burnham Park but - despite a pedestrian overpass - you cannot access this playground without crossing traffic.]
Burnham Park - 43rd Street Playground
This playground is new (as of 2023) and is a gem of a playground.
Williams- Davis Park - Playground
The 41st Street overpass leads directly into Williams-Davis Park which has a wonderful playground.
[At this point you would be extremely close to Holly Park and Mandrake Park but - sadly - both would involve crossing a street. So back to the lakefront trail.]
Edwin C. Berry Playground
You can skip the 35th Street overpass - it doesn't lead to any playgrounds - and head right for the 31st Street Beach and the Edwin C. Berry Playground. One of the best parks in the city.
Even though the lakefront trail continues uninteruppted (i.e. without crossing an access road or parking lot) until McCormick Place, there are no more playgrounds accessible via this route.
So, following these arbitary rules, the maximum numbers of playgrounds possible to visit in this area without crossing a street is 6.