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Madison, Wisconsin

This big college town is rich in history, stunning parks, and Insta-worthy architecture. The Winters are super snowy (fun fact: pretty much everyone drives a Subaru to navigate the icy roads), but the Summers bring out nature enthusiasts. Hit one of the city's award-winning parks, shop along Willy Street, or grab a beer at one of their many local breweries. Through June and July, head to the King Street corner of Capitol Square with a packed picnic basket and listen to live music on the square, and make sure to bring some of that delicious local cheese.