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A maze of rooms connects in the basement of the historic India Club to form two facets of Harry’s: a boisterous café on Stone Street and a classic chophouse in a former wine cellar off Pearl Street. The subterranean scene of the steakhouse feels so clandestine and high-powered, it’s almost like dining amid a Skull and Bones meeting. Post-work financiers sip whiskey at the low-ceilinged bar, while the ebony-paneled dining room—with murals of imbibing monks—and the brick-arched “grotto room” draw big-budget business lunchers. Some insider tips: Start with the sweet and smoky homemade Canadian bacon, which resembles a mini pork chop, or the fresh-lump-crab cocktail with a mellow old-bay mayo. Best options for entrées are the rib steak—aged on the premises for 28 days, it arrives with a charred crust and tender, flavorful meat—and the pork shank, a heaping, moist, and meaty carcass with a crackling layer of skin. Hash browns are a better pick than the bland creamed spinach as a side. And while the check is fitting for bull-market times, portions are a bear to finish, making it all well worth the investment in the end. — Kathleen Squires

Homemade Canadian bacon, $8; rib steak, $46; hash browns, $7.50.