Sample high-low food and cocktail pairings, like a short-rib panino alongside the bourbon-and-absinthe-based Vincent’s Ruin, at the Patterson House. The $11 drinks are obsessively crafted—homemade bitters, fresh-squeezed juices, custom ice molds from Japan—and small plates and snacks are made to order, from potato chips to fresh-from-the-fryer doughnuts ($5 to $11).
Arrive before 6:30 to snag a seat at the laid-back but thronged City House, a Germantown outpost for house-cured charcuterie, fresh pastas, and wood-oven-fired pizzas. Chef Tandy Wilson makes most of the ingredients in-house, including the lonza (pork salami) and mozzarella ($9 to $24).
Call a day ahead to reserve a seat on the second-story rooftop patio for skyline views at Watermark Restaurant, located in the up-and-coming Gulch neighborhood. The spot specializes in reimagined Southern comfort food, like soufflé-style goat-cheese grits ($8).