Series kickoff/Latin Night Celebration for the On the Water's Edge Concert Series at the Leonardtown Wharf (sponsored by Jimmy Hayden of RE-Max 100 and Homes for Heroes) in honor of International Dance [and Music] Day and Cinco DeMayo. The evening includes Leonardo Garcia Y Son Horizonte in concert and Latin Dance instruction.

The Leonardtown Summer Music Festival Presents The Lucky Few in Concert at the Port of Leonardtown Winery on Saturday, May 27, 2023 from 3 PM - 6 PM. Sample award-winning wine while enjoying the high-energy mix of popular rock and pop hits from this dynamic Southern Maryland band.




 

The 3-day weekend of the 23rd Annual Potomac Jazz & Seafood Festival kicks off on Friday, July 7, 2023 during Leonardtown July First Friday, with a FREE performance on the Leonardtown Square from 6 PM - 9 PM feat. the astounding Eric Byrd Trio!


 

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End of Summer Bash and Back to School Drive/Teacher & School Support Staff Appreciation Day at the On the Water's Edge concert series at the Leonardtown Wharf (sponsored by Jimmy Hayden of RE-MAX 10 and Homes for Heroes) featuring The Revival from 5 PM - 6 PM and The Dynamos from 6 PM - 8 PM. 

The Leonardtown Summer Music Festival presents Unfinished Business at the Port of Leonardtown Winery on Saturday, September 23rd from 3 p.m. - 6 p.m. Enjoy the laid-back vibe as they perform popular rock and country hits while sampling award-winning wine.

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown Cinco De Mayo First Friday. Performer Justin Allen from 6 PM - 9 PM.


 

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Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown First Friday. Performer: Joseph Norris from 6 PM - 9 PM.









 

Doc Martin & the Flannels, a high-energy band from Baltimore, MD, performs in Leonardtown Square for the first time for the Leonardtown Summer Music Festival on Saturday, July 15, 2023 from 8 PM - 11 PM.



 

Improvisational Jazz Guitarist, Jan Knutson, performs in Leonardtown Square for the first time for A&E First Friday. Enjoy smooth jazz and art related activities throughout the evening.




 

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown Octoberfest First Friday. Performer: Funkzilla SOMD from 6 PM - 9 PM

The On the Water's Edge Concert Series at the Leonardtown Wharf (sponsored by Jimmy Hayden of RE-MAX/100 and Homes for Heroes) presents a Bluegrass Celebration in honor of Armed Forces Day featuring the U.S. Navy Band Country Current (performing from 3 PM - 4 PM) and Jay Armsworthy (performing from 4 PM - 6 PM) on Saturday, May 20, 2023. Local student, Bethany Yeh, will open the event by performing the National Anthem.




 

R&B Celebration featuring The Rise Band & Show from 5 PM - 6 PM and Latrice Carr from 6 PM - 8 PM On the Water's Edge at the Leonardtown Wharf (sponsored by Jimmy Hayden of RE-Max 100 and Homes for Heroes). The evening also includes R&B line dance lessons with Renee Stephens.

 

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown First Friday. Performer TBA





 

The On the Water's Edge Labor Day Finale Concert, sponsored by Jimmy Hayden of RE-MAX 100 and Homes for Heroes, at the Leonardtown Wharf featuring John Zimmerman from 5 p.m. - 6 p.m., Girl Crush from 6 p.m. - 7 p.m. and Phillip Michael Parsons from 7 p.m. - 9 p.m.

Vertigo Red, Maryland's premiere rock cover band, performs in historic Leonardtown Square for the season finale of the Leonardtown Summer Music Festival on Saturday, October 14th from 8 PM - 11 PM.