Sean Josephs had been a restaurant wine buyer when he teamed up with Michael Tsoumpas, an American whiskey collector, to open Char No. 4 in 2008. The restaurant brought bacon, Kentucky Bourbon and Tennessee whiskey together in Cobble Hill, well north of the Smoky Mountains or the Ohio River port town of Maysville, believed to be the site of the first Kentucky distillery. Now Maysville, along with the distillations of more than 170 American masters working in wheat, rye, corn and blended American whiskeys, has settled into Manhattan. Located on a block in the upper Flatiron district of wholesale trinkets and sari shops, the restaurant joins NoMad and the Ace Hotel’s Breslin in transforming this neighborhood into a culinary mecca. Josephs hired Kyle Knall, late of Gramercy Tavern, to riff on smoke in food, and not just to satisfy the whiskey buffs at the bar. Knall’s food is subtle and complex enough to warrant an investment in one of the bottles off Josephs’ extensive wine list. Consider the subtleties of smoke in a Raveneau Chablis Valmur 1998, a Leflaive Bâtard 1999 or Drouhin’s Montrachet Marquis de la Guiche from 1993. These Burgundies have a place with Knall’s slow-roasted arctic char over cabbage, parsnips and mussels. The smoked trout is made for riesling, especially one of the J.J. Prüms, von Schuberts or Dönnhoffs from the 1980s and 1990s. If you stop in for lunch, try the grilled fish sandwich with Pépière’s Muscadet, or kale salad with duck confit alongside Sunier Fleurie. It’s the sort of menu and wine list that will keep you coming back for more, especially if you like to start your evening with a one-ounce taste of Lincoln Henderson’s Angel’s Envy or a small-batch Bourbon from Hirsch.
April 2017: A southern watering hole just north of the Flatiron Building, Maysville may be best known for its extensive American whiskey collection, but the wine list is one of the city’s unsung gems. Sean Josephs—who now divides his time between New York and New Orleans, where he and his wife, Mani Dawes, run Kenton’s—floats a highly personal wine list packed with well-aged Burgundy for the whole smoked trout, and Rhône and Barolo picks at excellent prices. —Tara Q. Thomas