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Tucked away in Grand Central Station, this classy lounge is the restored private office of early twentieth-century tycoon John W. Campbell. On weeknights, the 2,000 square foot space is a bit overrun with commuters grabbing a Prohibition Punch or the signature Terrace Punch before catching the train home. It’s more fun to go on the weekends or closer to closing time when you can get a seat and sip your Scotch while you pretend you’re in a Hemingway novel. Any night of the week, though, a sneakerless crowd can nosh on a small list of pricey “Cocktail Accompaniments,” like the artisanal-cheese plate; there are also free baskets of popcorn from the vintage popcorn machine. The more recent addition of the Campbell Terrace—an extension of the bar’s elegance to the outdoor portico on Vanderbilt Avenue—looks like a version of your grandparent’s living room: mahogany rocking chairs, wicker tables, and comfortable upholstered furniture. — Abbe Benson and Asheley Victoria

Couples who book this former office and salon of a twenties business tycoon will enjoy plush couches, clubby paneling, and a massive stone fireplace, plus gourmet cuisine courtesy of ubiquitous caterer Abigail Kirsch. The swank space comfortably accommodates up to 75 seated guests and 125 for cocktails. From $150 to $500 per person.