Funkzilla SOMD

Memorial Weekend Bash featuring the Funkzilla Band On the Water's Edge at the Leonardtown Wharf. Nightcap opens the show from 2 p.m. - 3 p.m., then Funkzilla performs from 3 p.m. - 5 p.m.

Latrice Carr

R&B Celebration featuring N2N Band's Motown Celebration from 5 PM - 6:30 PM and the Latrice Carr Band from 6:30 PM - 8:30 PM On the Water's Edge at the Leonardtown Wharf. The evening includes R&B Line Dancing Lessons with Renee Stephens.

Eric Byrd Trio

The 3-day weekend of the 22nd annual Potomac Jazz & Seafood Festival kicks off on Friday, July 8, 2022, with a FREE performance on the Leonardtown Square from 6:00 p.m. - 9:00 p.m. of the astounding Eric Byrd Trio!

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Leonardo Garcia
Y Son Horizonte

Award-winning Leonardo Garcia Y Son Horizonte returns to perform at Leonardtown Cigars (40955 Merchants Lane #14, Leonardtown, MD 20650 ) for a Havana Nights Party (part of the Latin Nights in Leonardtown series). Enjoy live music, salsa and Kizomba dance lessons, open dancing, food, specialty drinks and fine cigars. This is a music festival signature event. Tickets are $35/pp and include open dancing, dance lessons, food from Salsa's Mexican Cafe, and a complimentary glass of Mojito or Cuba Libre.
Limited tickets available.

Purchase Tickets Here

Blazin' Keys

Blazin Keys Dueling Pianos takes the stage in Leonardtown Square. Enjoy a summer cookout with The Rex Restaurant & Bar and ice cream from Frog Town Ice Cream shop (Frog Town is providing free ice cream to kids who attend the event). FREE shuttle rides from Patuxent Transportation will be provided throughout Town from 10 a.m. - 10 p.m. (for information about the Trolley route and schedule visit - Leonardtown Trolley). Come early and enjoy a pre-show featuring Justin Allen at The Rex from 1 p.m. – 4 p.m. and save time to dine or browse our local shops before the main event in the Square.

Flippin' Eyelids

End of Summer Bash and Back to School Drive On the Water's Edge at the Leonardtown Wharf featuring Flippin' Eyelids and Doc Lohn at new time: 4 p.m. - 7 p.m.

Josh Airhart

Sample award-winning wine and slushies as you kick back and relax at the Port of Leonardtown Winery while listening to the smooth sounds from Josh Airhart & the Foundation. 

Higher Standards

Higher Standards returns to perform in Leonardtown Square for A&E ArtWalk First Friday. Enjoy dining alfresco at one of the restaurants or bring a blanket or lawn chair to enjoy  smooth jazz in the Square.

Robbie Boothe

Labor Day Weekend Bash On the Water's Edge at the Leonardtown Wharf featuring the Robbie Boothe Band, the Billie Breslin Band and John Zimmerman.

Justin Myles, Wes Ryce,Greg Barrick & David Hamner

Sample award-winning wine and slushies as you kick back and relax at the Port of Leonardtown Winery while Enjoying a great mix of rock and Country music from Justin Myles, Wes Ryce, Greg Barrick & David Hamner

Reagan Years

The original 80's Tribute Band takes the stage in Leonardtown Square for the Finale of the Leonardtown Summer Music Festival.

The Bootleggers

The Bootleggers will be performing at the Fenwick Inn on Sunday, September 18th from 4 p.m. - 6 p.m. Gates open at 3:30 p.m. Please bring a blanket or lawn chair to enjoy the show. There will be a cash or credit bar during the show!

HydraFX

HydraFX will entertain the crowd once again at the 2nd Annual Octoberfest Celebration in the Brudergarten at Shepherd's Old Field Market.