Enjoy dinner at one of the many local restaurants, grab a drink from Social Coffeehouse or Antoinette’s Garden, explore Shepherd’s Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates; the Old Jail Museum will be open for tours and the SoMar Drum Circle performs in the town square (7pm). Stop by the Port of Leonardtown winery for a tasting, a treat from Deutsch-Mex & Noli’s Cannoli Bar and live music with Billy Yeager (5:30-8:30pm). 5-8pm, downtown Leonardtown: http://firstfridaysleonardtown.com/.