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From Cleveland to Milwaukee: The allure of the mid-size city —

Maggie, a fashion stylist and my Airbnb host in Milwaukee, stuffs a biking map and tourist guide to the city into my hands. Her two adopted Boston terriers wiggle and pant at my feet.

“You’re gonna have a great time here,” she promises. “It’s a fun town.”

I thank her, somehow balancing the maps and books atop my armful of luggage.

“To tell you the truth? I’m really liking the mid-size cities anymore,” she says, sounding almost embarrassed by her confession.

Then she drops her voice even lower. “I kinda like it even better than… Portland.”

I can tell she’s bracing herself for my gasp. To prefer a city such as Milwaukee to Portland? The epicenter of all that is sustainable and urban and hip? Sacrilege!

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