Leonardo Garcia
Y Son Horizonte

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 Lucky Few

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 a high-energy mix of popular rock and pop hits from this dynamic Southern Maryland band.

Doc Martin & the Flannels

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 7 PM - 10 PM. This event, as well as the Summer Bar Crawl, are being held in honor of local fallen hero, Brice Trossbach (participating businesses in the Bar Crawl are accepting donations for the family- Learn More). Backup rain location for the concert: The Rex Theatre, 22695 Washington St, Leonardtown, MD 20650

The Dynamos / The Revival

End of Summer Bash and Back to School Drive 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.

Unfinished Business

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. Sample award-winning wine, and enjoy the laid-back vibe as they perform popular rock and country hits.

May First Friday

Enjoy live music featuring Justin Allen from 6 p.m. - 9 p.m. and activities with Leonardtown artists and businesses during Leonardtown's Cinco De Mayo First Friday. 








 

June First Friday

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown First Friday. Performer: Joseph Norris.





 

August First Friday

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown First Friday. Performer:
Dave Norris

Dr. Ceylon Mitchell and
Jan Knutson

Enjoy live music from contemporary flutist, Dr. Ceylon Mitchell, and improvisational jazz guitarist, Jan Knutson, in historic Leonardtown Square during Arts & Entertainment First Friday on September 1st from 4 p.m. - 7:30 p.m. This exciting, annual event celebrates the anniversary of Leonardtown being named an Arts & Entertainment District (this year Leonardtown celebrates its 10th anniversary). 

October First Friday

Enjoy live music and activities with Leonardtown artists and businesses during Leonardtown Octoberfest First Friday. Performer: Funkzilla SOMD

Jay Armsworthy / U.S. Navy Band Country Current

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.

Eric Byrd Trio

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 5 PM - 7 PM featuring the astounding Eric Byrd Trio!

Latrice Carr /
The Rise Band & Show

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 Stevens. New Date: This event has been moved to Friday, August 11, 2023 from 5 p.m. - 8 p.m. due to forecasted rain on original date of June 24th).

Phillip Michael Parsons / John Zimmerman / 

Girl Crush

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 3 PM - 4 PM, Girl Crush from 4 PM- 5 PM and Phillip Michael Parsons from 5:30 PM - 7:30 PM. The winners from the Sidewalk Art Contest, held earlier in the day from 10 AM - 5 PM, will be announced at 5 PM. Then stick around after the concert for a fireworks spectacular being held in honor of Leonardtown's 10th Anniversary as an Arts & Entertainment District, starting at 8 PM

Vertigo Red

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 7 PM - 10 PM.