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Milwaukee has had its share of visitors, starting with French missionaries and explorers in the late 16th century. Now to that list you can add Time Out Chicago, which does road trip recommendations this week. I have to take their word for Milwaukee's charms, not knowing the city well, but they did miss the best reason to go to there. Probably because it's not in Milwaukee.
On the way there or back, between Racine and Kenosha on Hwy 32, you'll see this:
You don't have to know anything about vernacular architecture to know that the HobNob is going to be the best bar in the world. It was built in 1953, and it probably hasn't changed much since. It's got white leather furniture, mirrors, a view of the lake, bow-tied bartenders, and a leather pad running the length of the bar--I Like Ike flyover glamour at its best. I didn't have a chance to sample the food, but I do recommend the piano bar on Saturdays with Lillian.