North Lakefront Trail

This is the third installment of the series answering the question:

How many playgrounds can you visit without crossing a road?

The rules are simple: what's the longest tour you can take without crossing a road, street, driveway, boulevard, or other car-centric pathways? This tour starts on the north side of the lakefront trail.

Heading south, immediately, this route faces issues near Foster Avenue when the bike trail cross Simonds drive (the awkward road/parking lot combination). So, strictly speaking, these three  playgrounds are off limits and you would be forced to stay on the walking path closest to the lake to avoid these crossings.

Playground

Lincoln Park - Hersh Playground

Hersh Playground is on the west side of DuSable Lakeshore Drive but is accessible via a pedestrian underpass.

Staying by the lake and using the pedestrian underpass, you can get to the next playground in Lincoln Park near Montrose.

Here, again, your direct route is blocked by the two street crossings just south of the tennis courts. But - in reckless disregard to the self-imposed rules - you continue south, you could continue to the Boat Playground near Roscoe and then using the underpass just south of Belmont would lead you the next two Lincoln Park playgrounds.

Having thrown caution to the wind, the next two playgrounds in Lincoln Park would definitely involve some street crossings but could be do-able. But I think you could travel all the way south and access the Lake Shore Park playground via an underpass.

In terms of officially following the rules of avoiding any and all street crossings, this route does relatively poor. But if you can tolerate a few relatively quiet street crossing, the North Lakefront Trail provides access to a string or really great playgrounds.