Joe Sugarman

Cup o' Joe

Food, travel, and news on the Chesapeake Bay



St. Michaels’ Speakeasy

Stopped by Rupert’s Bar and Tea Room for a plate of meatloaf and mashed potatoes and a glass of Malbec on a recent wintry night. Don’t get me wrong—this is no diner-like greasy spoon. In fact, it’s one funky restaurant, with jazz on the speakers and a menu that wanders from the aforementioned meatloaf to a curry of the day to a Moroccan tagine. There’s also a good list of small plates (smoked trout with horseradish sauce) and interesting salads with intriguing names, i.e., the “Kinky,” a ménage a trois of cheeses on a bed of greens. (Good luck ordering that on a first date!)

The petite restaurant has three rooms downstairs: a glittering bar, with candles and Interview Magazine cover lithographs mounted on its walls; a cozy middle room with a fireplace and leather lounge chairs reminiscent of an English study; and the polo room, which is decorated with horsey prints and a set of mallets. Upstairs features a 16-seat communal table and a way-cool bar made from a cut-away hot-air balloon basket.

The overall effect is a kind of speakeasy, St. Michaels-style. I’ve heard the place can get boisterous around closing time, with locals visiting each other at adjacent tables for one last glass of wine.

Oh, and if you like the table at which you’re dining, check the price tag: Most of the antique furniture is for sale, courtesy of owner Marianne Yost, who doubles as the proprietor of London antiques shop just down the street. 407 S. Talbot Street, Saint Michaels, 410-745-9090

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