Upcoming Event

First Friday Weekend in Leonardtown

Oct 7 - Oct 9

  • Admission: Free
  • Location: Leonardtown

During the weekend, come to Leonardtown for the Fall Fest Celebration. Businesses are celebrating Fall Fest with themed events, performances, exhibits, and special discounts in Southern Maryland's only designated Arts and Entertainment District. Begin your weekend in Leonardtown, taking in everything the town has to offer.

Art aficionados are encouraged to immerse themselves in local art at North End Gallery, The Craft Guild Shop, New View Fiber Works, and the St. Mary's Arts Council Gallery and Gift Shop, and, if you're feeling extra artsy, stop by The Yellow Line or Board & Brush to create your own masterpiece. If you're in the mood to shop, get lost among the many treasures at Shepherd's Old Field, the stacks of books, music, and more at Fenwick Street Bookstore, or at any of the other unique local shops. When you get hungry, Leonardtown offers an array of distinct dining establishments where you can wine and dine your last weeks' worries away, from the upscale casual vibe at Sweetbay to the historic hometown hospitality of the Front Porch. And if wine is your jam, check out Antoinette's Garden or the Port of Leonardtown Winery, where they often host live music and local food trucks. Wonderfully walkable historic downtown Leonardtown is always teeming with activity, but on First Friday, they turn it up to eleven!




First Friday Weekend in Leonardtown

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