Victorian mansions, tree-lined streets, upscale business districts. Welcome to Shadyside: Pittsburgh’s permanent valedictorian. This smarty-pants of a neighborhood is home to some of the most affluent residents in the city, and offers a swift stroll to three universities — Carnegie Mellon, Pitt, and Chatham — as well as three private schools. Literal white picket fences aside, don’t let Shadyside’s 19th-century charm and meticulously manicured lawns fool you. Sure, there are wholesome boutiques and homemade ice cream and high-end furniture shops by day. But after dark, this spot’s inner party gal makes her rounds, drawing the late-night crowds into any number of taverns along three primary business hubs: Walnut, Ellsworth, and South Highland. Once you’ve walked or biked your way through the neighborhood’s less-than-one square mile, go ahead and treat yourself to the best damn cake in America. This one’s on us.


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