Town’s First Friday Weekend Celebrates Hometown Heroes

First Fridays open up Leonardtown, MD, for a one-of-a-kind shopping and entertaining evening, and invite visitors to join in some fun June 6-8. The theme will be Hometown Heroes Weekend.

The town honor will honor its Hometown Heroes with a celebration in the Leonardtown Square from 5 to 9pm Saturday, June 7. The Robbie Boothe Band and all of its members have decided to come out of retirement for a one-night event. The Deadrise (Max and Sammy’s band) will kick off the evening from 5:30 to 6:15pm.

First Fridays usually offer specials at participating shops and restaurants, open studios and workshops at the art studios, opening receptions at the galleries, and much more.

At the North End Gallery, check out the June show “Geometry,” which will run until June 29. The opening reception will be 5 to 8pm June 6.

Art aficionados are encouraged to immerse themselves in local art at 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.

Join the Arts Council on First Friday June 6 for an audience participation drum circle from 5 to 6pm for June, July, August, and September 2025. These free events are open to all ages and skill levels. Bring your percussion instrument or use one of theirs. Location: lawn adjacent to the council’s office at 22660 Washington St. Find the SoMar Drummers indoors in the event of rain or excessive heat. Stay for the whole time or drop in as you like.

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 past 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. Check out the changes at The Rex on the Square. The town welcomed a new seafood restaurant in February, T&J’s Cove at 41565 Park Ave.

Go to the Leonardtown First Fridays Facebook page for details about specific events in downtown, midtown, and uptown as they are announced.

Visit www.VisitLeonardtownMD.com for a listing of shops and restaurants. Visitors are advised to contact desired locations for specific hours and event information.

The St. Mary’s County Historical Society is the repository of a unique collection of Maryland memorabilia and museum pieces displayed on the first floor of Tudor Hall and in the Old Jail Museum at 41625 Courthouse Drive in Leonardtown. The 18th-century Tudor Hall also serves as headquarters of the society and houses the Historical Society’s Research Center.

To learn more about the St. Mary’s Historical Society, visit its Leader member page.