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leonardtown summer

music festival

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Thank you to everyone who joined us throughout the 2022 for the Leonardtown Summer Music Festival. It was a wonderful season of music, dancing and fun! A heartfelt hank you to the amazing performers and our kind sponsors, partners and volunteers who helped make it happen, and a special thank you to Jimmy Hayden of RE-MAX 100 and Homes for Heroes for helping to create the On the Water's Edge series at the Leonardtown Wharf. The Wharf concerts were an astounding success! Please visit this page for news and announcements about this season or join the Leonardtown A&E News Email List for advanced notice of upcoming concerts and events! 



May 28th
2 PM - 5 PM

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.

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June 11th
5 PM - 8:30 PM

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.

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July 8th
6 PM - 9 PM

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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July 16th
6 PM - 9 PM

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

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July 23rd
6 PM - 9 PM

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.


August 20th
4 PM - 7 PM

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.

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August 27th
4 PM -7 PM

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. 

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September 2nd
5:30 PM - 7:30 PM

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.

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September 3rd
3 PM - 7 PM

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.

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September 17th
2 PM - 5 PM

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

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October 14th
6 PM - 9PM

Reagan Years

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

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September 18th
4 PM - 6 PM

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!


October 1st
6 PM - 10 PM


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


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