Join us to “walk the walk” on First Friday, September 3rd from 5-8:30 PM! This special evening will celebrate Downtown Leonardtown’s eighth year as an officially designated Arts & Entertainment District of Maryland. A highlight of this event will be the annual Art Walk contest, an exciting opportunity to view locally created work in a wide variety of media and styles.

Winners of the Art Walk contest will be selected by popular vote so be sure to bring your friends, grab a ballot at any participating shop, walk around town to choose your three favorite artwork entries, and cast your votes! Submit your ballot at St. Mary’s County Arts Council for a free small gift, or just drop it off at any of the participating businesses.

The voting period will open on September 1st and will run through the whole month, ending on September 30th.

Also awarded will be a $25 gift card from Shepherd’s Old Field Market and a $25 gift card from Social Coffeehouse to lucky voters selected at random (one entry per person, all ages may enter, no purchase necessary).

Other fabulous featured activities at Leonardtown Square will include: hands-on art activities, plein air painters, and much more!

Featured specials include:

  • Higher Standards – jazz band – playing from 5:30 to 7:30 PM at Leonardtown Square
  • North End Gallery – celebrates their 35th Anniversary from 11 AM to 8 PM w/ a special reception from 5-8 PM!
  • Old Jail Museum – will be hosting free tours from 10 AM to 7 PM, the Leonardtown Visitors Center is also located at the museum.
  • Shepherd’s Old Field Market will be offering a variety of shopping opportunities from over 70 different stores and services, their new ice cream shop The Salted Scoop will be open also!
  • Free Trolley Rides from 4 to 10 PM! Info on the Town of Leonardtown Facebook page.

Make it an overnight stay at The Inn at Leonardtown, newly renovated and located in Downtown!

Shops and restaurants will be open late for dining, desserts, and more! There will be something for everyone of all ages and interests!

Check the Leonardtown First Fridays Facebook page for details about specific events in Downtown, Midtown, and Uptown as they are announced, we look forward to seeing you!

Also be sure to check out for a comprehensive listing of shops and restaurants as there will be many more open besides those listed above.

Please contact desired locations for specific hours, COVID-19 safety guidelines, and event info. Also see the events section at the Visit St. Mary’s County website for additional info about these and other upcoming local events in the area.

A huge note of appreciation to the Town of Leonardtown, the St. Mary’s County CommissionersLeonardtown Business Association (LBA) members, the SoMar Drummers and the First Friday volunteers for their assistance with these events.

We are especially appreciative of the support from our LBA Platinum Sponsors (Cheseldine Tire & AutoLeonardtown Chevy Buick GMCMarrick HomesQuality Built HomesSt. Mary’s County Arts Council, The County Times, & Visit St. Mary’s) who all have contributed to make First Fridays a wonderful community event.

#LeonardtownFF #VisitLeonardtown

Line dancers photo by Brandy Blackstone.

Plein air painter photo by Michael Montillo.

Other photos by Jenn Dorsey, Higher Standards photo provided by band.