May 30, 2026

First Friday in Leonardtown Oct. 3

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in some Octoberfest fun October 3-5. Take the Scarecrow Stroll. Come to town from Oct. 3-26 to see the scarecrows displayed all over town and then vote for your favorite.

At the North End Gallery, check out the new show, “Small Gems,” with artists Susanne Jantsch, Barbara Rushworth, and Suzanne Shelden. The show will run September 30 through November. The opening reception will be 5 to 8pm October 3.

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 for an audience participation drum circle from 5 to 6pm. The free event is 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.

Leonardtown now has a mobile app called Hello Leonardtown that provides information about town news, events, service interruptions, and updates. The app is available for download in the Apple Store and Google Play Store. Call 301-475-9791 for more 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.

(Pixabay photo by Charles Parker)
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