Kim Hairston, The Baltimore Sun
Chick & Ruth's Delly, 165 Main St., Annapolis, 410-269-6737, chickandruths.com
Long a go-to spot for Maryland politicians, this bustling eatery has attracted a whole new clientele with its six-pound milkshake and "Colossal Shake Challenge." "We use half a gallon of milk and the shake itself is 119 ounces," says proprietor Ted Levitt (pictured), who serves the drink in a huge glass bowl with 13-inch-long straws. "A lot of the midshipmen from the Naval Academy and other area college kids enjoy challenging each other."