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I've developed a rough proposed route, starting from last month's unused Green route and lopping off chunks.
It's under 20 miles, passes through several parks (Grant, Douglas, Garfield, Humboldt, Lincoln), and ends at any desired point on lakefront North of Fullerton as far as Diversey or Montrose. Would be nice to not stay straight on Roosevelt nor North nor Fullerton so long, and is the Grant Park portion allowed?
See proposed route in Google Maps
Instead of the long trip west on Madison, I'd go a block south at Damen and continue west on Monroe. Monroe is a pretty tree lined residential street while Madison there is a divided industrial street. Monroe has traffic calming roundabouts and ends in cul-de-sac at Western eliminating most car traffic. However, the slight curb of the cul-de-sac is easily negotiable by most bikes and those that can't can take a driveway cutout onto the sidewalk for a block.
This route also takes us past some pleasant urban renewal and some vacant lots which I believe date back to the riots after MLK's assasination in 68. And it takes us past the site of Fred Hampton's murder in 69. Fred's family filed a wrongful death suit against the city, state and federal governments and over a decade later won a $1.85 million settlement. The Chicago city council honored Fred with a declaration of a "Fred Hampton day" in 1990. All of this ties in with a similar ongoing miscarriage of justice orchestrated against fellow former black panther Mumia Abu Jamal who has spent more than half of his life sitting on death row. Our ride will be on his birthday.
Anyway back to the map, at Western I suggest going south a block to Adams and then taking Adams west. It is also a pleasant low traffic residential street. It has an interesting discontinuity at Sain Park, perhaps one of the most neglected little parks in the city and it provides a stark contrast to the other parks we will be riding through. After crossing or skirting Sain Park we can continue west on Adams because these breaks to auto traffic mean we aren't tieing up traffic ourselves.
Adams ends at Sacramento. A half block jog north will put us at 5th Avenue and back on your route.
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