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Old Homestead is even older than Keens and every other steakhouse on this list, having been in operation since 1868. The three-story space is on the Chelsea/Meatpacking border, and the menu is huge. You can choose from over 15 different steaks, but there are two we recommend trying. The Porterhouse here is cooked and seasoned very nicely, though it didn't knock our socks off. We actually like the ribeye here best of all. It's tender, has a ton of flavor, and pairs well with the excellent garlic mashed potatoes and creamed spinach. Finish your meal with the Drug Store Old Fashioned Sundae. The combination of walnuts, chocolate syrup, whipped cream, and really good vanilla ice cream to make the kind of dece