The town earned that state designation back in 2013, and it shows — working galleries like North End Gallery, the St. Mary’s County Arts Council gallery, and studios wovenright into downtown storefronts. First Fridays bring free live music and art to the Square every single month. Year-round, 5–8 PM on the first Friday of the month, downtown Leonardtown fills up with live music, art openings, drum circles, and family activities — all free. First Friday turns into a full ArtWalk, and the town runs a free trolley for bigger event weekends. The Wharf in Leonardtown is home to events year round, often including live music and food trucks.