Chick & Ruth’s Delly
Family-owned and operated since 1965, Chick and Ruth’s Delly is a local dining landmark. Located in the heart of historic downtown Annapolis, the cozy, kitsch deli is known for its delicious diner food. The menu features everything from breakfast fare, pizzas, burgers and its legendary piled-high sandwiches. Particularly hungry guests may want to take on Chick & Ruth’s Man vs. Food Challenge where consuming a six-pound milkshake and a colossal one-and-a-half-pound burger or sandwich within one hour wins daring diners a t-shirt. But if you try just one thing, make sure it’s Chick & Ruth’s jumbo lump crab cakes as they’re often hailed as the best in Maryland.