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FREE outdoor concerts at the Wharf, Leonardtown Square and other locations around Town!

2024 Leonardtown Summer Music Festival


April - October 2024

Leonardtown hosts a summer of exciting concerts from April - October 2024 throughout the Town from historic Leonardtown Square to picturesque Leonardtown Wharf and beyond! Enjoy a variety of live music, dancing, great food, drinks, and more throughout the season.

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On the Water's Edge Concert Series

At Leonardtown Wharf

The Town of Leonardtown and the Leonardtown Business Association are proud to present the On the Water's Edge Concert Series at the Leonardtown Wharf (sponsored by Jimmy Hayden of RE-MAX/100 and Homes for Heroes).

Come by water or land - Bring your lawn chair or blanket and enjoy live music, sample award-winning wine from Port of Leonardtown Winery, purchase beer from the Leonardtown Volunteer Fire Department tent, and cool down with sweet treats from Frog Town Ice Cream.

Leonardtown Wharf,

22510 Washington Street

Leonardtown, MD 20650


Third Tuesday Tunes

In Leonardtown Square

Escape the midweek monotony and immerse yourself in the enchanting melodies of live acoustic music in Leonardtown Square! Join us for "Third Tuesday Tunes," a musical oasis that transforms lunchtime into a soulful and vibrant experience. Brought to you by the Town of Leonardtown and Jimmy Hayden of RE/MAX 100 and Homes for Heroes

Talented local acoustic artists will serenade you with an eclectic mix of tunes, creating the perfect backdrop for a relaxing and enjoyable break from your day. From classic hits to contemporary favorites, there's something for everyone to enjoy.

Leonardtown Square,

22670 Washington Street

Leonardtown, MD 20650


Square Concerts

In Leonardtown Square

The Town of Leonardtown and the Leonardtown Business Association partner together to bring talented local bands to the Square. The large concerts happen in the heart of Town - Bring a lawn chair or blankets to enjoy the music. 

Leonardtown Square,

22670 Washington Street

Leonardtown, MD 20650


Sponsored by Jimmy Hayden of RE/MAX 100 and Homes for Heroes

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Latin Concert

Saturday, April 20th  5 p.m. - 7 p.m.

Trio Caliente unites and inspires audiences around the globe with their inimitable blend of Flamenco, Pop, and Latin Dance Music. Enjoyed by political luminaries stateside and abroad, notable Fortune 500 companies, and venerated international organizations, festivals and concert venues around the world, Trio Caliente delivers unique sound and style to any occasion– providing an unforgettable experience for your private event.

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4th at the Wharf Event & Concert

Thursday, July 4th
3 p.m. - 7 p.m.

Join us at the Leonardtown Wharf for an afternoon of contests, activities, yard games, tasty food, and a FREE live concert featuring Midnight Sunsets! This special event is brought to you by the Town of Leonardtown, the Leonardtown Business Association, and with the support of our generous sponsors, Jimmy Hayden of RE/MAX 100, Mattingley Gardiner Funeral Home, Town Market, and Earthwise Pet. Tasty eats, treats, and beverages available for purchase.

In addition to the concert, enjoy fun activities including a watermelon eating contest, dog parade, crab derby, ping pong, chess games, yard games and more!

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Season Finale Concert

Saturday, August 31st
5 p.m. - 8 p.m.

Join us for an exciting evening of music Labor Day weekend for the season finale of the On the Water's Edge Concert Series at the Leonardtown Wharf. We're ending the concert with a bang! Following the concert will be a fireworks extravaganza.

Music Lineup:
Six Gun South 5 p.m. - 6 p.m.
Copper Pennies 6 p.m. - 8 p.m.

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Military Appreciation Concert

Saturday, May 18th
5 p.m. - 7 p.m.

Cover Your Six, LLC is a veteran owned Rock/Variety Band delivering live music across several genres of music that encompasses a large portion of the past half century's greatest hits. Cover Your Six is a band composed mostly of military veterans (Marine Corps/Navy) and first responders (Police and EMS) and CY6 has been very active in the community raising money and reaching out to other veterans and first responders in need using the power of music to help the cause. Cover Your Six is proud to be a Southern Maryland band. You can find the members of CY6 working on the first responder front lines or rocking out all over Maryland, but they are always out there, Covering Your Six!

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R&B Concert + Teacher Appreciation

Saturday, August 10th
5 p.m. - 7 p.m.

The N2N Band is a highly motivated group of exciting musicians who spends hours bonding and creating quality music. The N2N Band originate with six members and now performs throughout the DMV with eight highly skilled musicians with nothing but the desire to create and perform music of all genres. Over the past 15 years, the band has headlined a number of events to include a Presidential Inaugural Ball. The N2N Band has opened for grammy award winning artist BeBe Winans and national recording artist The Delfonics. Our eight members band offers a wide array of old & new school R&B, Soul, Pop and Motown music to our clients. The band's core can expand to a full horn section upon request to include a sax, trumpet and trombone.

On The Waters Edge


Sponsored by Jimmy Hayden of RE/MAX 100 and Homes for Heroes

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Tuesday, April 16th
12 p.m. - 1 p.m.

Becky Titus is a Southern Maryland native who performs indie rock covers and original music. She can be seen performing at local venues with fellow musicians as well as with the new pop rock duo, Titus & Simpson, established with her musical partner Carla Simpson.




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Tuesday, June 18th
12 p.m. - 1 p.m.

Billy Breslin has been playing guitar and polishing his craft for over forty years. After his tour in the U.S. Marines, Billy attended Frostburg State University where he began performing at local venues and established his band "The Swamp Weasels." In the 90's the band opened up for many country artists and enjoyed a loyal following while playing many clubs in the D.C. area. He usually appears solo, but still does several shows with his band each year.

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Tuesday, May 21
12 p.m. - 1 p.m.

Chris Dean is musician, guitarist, teacher and live entertainer residing in Southern Maryland. He has travelled the country playing lead guitar in various different groups including Phillip Michael Parsons, Any Given Sin, Ryan Montgomery, Josh Gracin, Jason Cross, Jae Jin and more. While Chris is not touring, he teaches music throughout Maryland specializing in guitar and music theory as well as offering piano, trumpet, banjo, and ukulele instruction. Chris is a father and in his spare time ,outside of music, he enjoys consuming various forms of media such as movies and comics and spending time with his son, friends and family. 

Photo credit: Jack Nutter

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Tuesday, July 16th
12 p.m. - 1 p.m.

Bio coming soon.

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Tuesday, August 20th
12 p.m. - 1 p.m.

Wildgood is a high-energy party rock/pop band based in Southern Maryland. We play popular rock, pop and country covers that get people dancing and singing - a great mix of songs from the 90's, 2000's, and today's music.

SQUARE CONCERTS in Leonardtown Square

The Town of Leonardtown and the Leonardtown Business Association partner together to bring talented local bands to the Square. The large concerts happen in the heart of Town - Bring a lawn chair or blankets to enjoy the music. 

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First Responder Fundraiser

Saturday, June 8th
5 p.m. - 7 p.m.

Nashville, be on the lookout. A non stop, high energy show, delivered by some of the best in the Mid Atlantic. Dedicated to their fans, and a commitment to excellence, RDR is becoming a household name. When you need your country fix, look no further.

Red Dirt Revolution is a Baltimore based high energy Country act with a driving dual guitar sound and pinpoint harmony vocals. Polished veterans of the music scene come together to produce a country band like no other. 

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Season Finale Concert

Saturday, October 19th 
7 p.m. - 10 p.m.

It's All Good is THE definition of a good time! As one of the Mid Atlantic's top cover bands, IT'S ALL GOOD brings contagious energy. From reimagined radio hits to timeless classics, their mashups will leave you excited for more!

Square Concerts
Third Tuesday Tunes
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