Thanks for the suggestions..will have to try those. I'm in downtown CHI quite often, as the company I work for has their main headquarters there. Plus it's not too far away and a great city to visit.
The UPAF Ride for the Arts in Milwaukee is nice. Several different lengths, we're doing the 50 mile one. There's a 75 miler, a 25 miler and a 5 or 8 miler. Fund raising ride for the United Performing Arts fund (i think that's the UPAF) - my employer is the major sponsor so we have a pretty big "team". Rode for first time last year, did 25 miler which ran south along the lake and through neighborhoods. Last year the two longer routes ran north, again lake, Oak Leaf Trail other streets. Well organized ride, with a festival after it on the Summerfest grounds.




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