In a pinch and based on geography, my party ended up at Harry's Bar and Tables in Westport - arguably the most universal of spots that pulls in a crowd ready to drink all manner of drinks. A dark and stormy (rum and ginger beer with a lime wedge) is never shyly poured, the wine seems classier when it's pulled from a cooler covered in leaded glass, and the beer is right down the middle. There are tables looking out on the most alive corner of Westport (Westport and Pennsylvania) and a patio that usually has a few seats open.
What other bars fall into the happy place between dive and closed-toes shoes required?
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