Leonardtown, MD— September marks the 9th Anniversary of Leonardtown receiving its designation as an Arts & Entertainment District. It holds the honor of being the only A&E District in Southern Maryland. The Town will mark the anniversary with a series of exciting events and happenings throughout the entire month of September including concerts, art shows, sidewalk art, Plein air events, and much more!

The festivities kick off with Art Walk 2022 on Friday, September 2nd beginning at 5 p.m. on the first night of the A&E First Friday All Weekend Celebration. Make your way to local participating businesses around Town to view fabulous artwork by local artists and vote for your favorite, then stop for dinner in Town at one of our fine restaurants before making your way to Leonardtown Square to enjoy live music provided by the Higher Standards Jazz Trio from 5:30 p.m. – 7:30 p.m.

The fun continues in LTown Alley on Park Avenue (across from the Good Earth Natural Foods Store), where we’ll be celebrating Leonardtown’s newest and most unusual mural titled, “Alice in Leonardtown” from 7:30 p.m. – 10 p.m. with balloon art, crafts and themed activities – golfing with pink flamingos courtesy of Above Par Golf & Entertainment, games with the White Rabbit character, and dress as your favorite Lewis Carroll character and have your photo taken with Leonardtown’s Alice (courtesy of Ron Bailey Photo Productions). Following the ribbon cutting, we will be screening the beloved animated classic movie about a young girl who goes on a WONDERous journey (can you guess the movie?). The movie will be shown against the stunning mural, created by talented artists Dan Ropp and Tom Rogers, which doubles as a movie screen. This event is the first of many fabulous evenings of outdoor movie screenings being planned.

Then on Saturday, September 3rd, the beautiful Leonardtown Wharf is the stunning location for a day of creativity and fun. The day begins with the 1st Annual Sidewalk Art Contest where local established and budding artists are invited to use the sidewalks at the wharf as the backdrop for their works of art. Register for FREE at LtownMD@gmail.com or brandy.blackstone@leonardtownmd.gov in one of four categories (Youth, Dabbler, Family or Pro) to participate for your chance to win over $400 in cash prizes and gifts. Participants will be able to work at their own pace by checking in anytime between the hours of 10 a.m. – 3:30 p.m. – taking as much or as little time as needed to complete their artwork. Judging is at 4 p.m., and the winners will be announced at 5 p.m. during the evening’s concert at the wharf.

The concert is the thrilling season finale for the On the Water’s Edge Music Series at the Leonardtown Wharf. This exciting series, sponsored by Jimmy Hayden of RE-MAX 100 and Homes for Heroes, is part of the Leonardtown Summer Music Festival. The finale, taking place from 3 p.m. – 7 p.m., is a Labor Day weekend bash featuring local favorites the Robbie Boothe Band, John Zimmerman and Billy Breslin. In addition to amazing live music, attendees can enjoy wine from Port of Leonardtown Winery, beer from Leonardtown Volunteer Fire Department, tasty eats from the Leonardtown Volunteer Fire Department Auxiliary, and sweet treats from Frog Town Ice Cream. As noted, we will be naming the winners of the Sidewalk Art Contest from earlier in the day during the concert at 5 p.m. (right before Robbie Boothe takes the stage).

These amazing events presented here are just a highlight of some of the signature events that are taking place during the Leonardtown Arts & Entertainment Month Celebration.

For more information about these and other exciting events taking place in September and to download the A&E Month Itinerary, visit: VisitLeonardtownMD.com/LeonardtownAE

. Join us in Leonardtown for Arts & Entertainment Month and discover what makes Leonardtown a Most Exceptional Place.


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