Best Neighborhood Bar: Sassafras
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As the demographics of neighborhoods like Oak Forest began to change in the last decade, so did the business that moved into the area. In the case of a rather quiet, industrial stretch along Pinemont, that meant Sassafras, a bar with its killer jukebox, pool table and hard liquor, owes about as much to hipster places like Big Star Bar (also owned by one of the partners here) as it does to your typical neighborhood hang.
But Sassafras also knows its neighbors. It has a well-considered wine and beer selection to go with arguably the best sangria in town. Nearby residents, quite a few of whom get there on foot, are regulars and its well-worn patio is complete with stray cat shelters and food bowls for the feral cats that roam freely. They certainly seem to get the Oak Forest vibe and, judging by the decent crowds on the patio nearly every night of the week, their neighbors approve.