
LEONARDTOWN, Md. – In the heart of Leonardtown, a unique collaboration between the town and local businesses is creating a vibrant sense of community – a dynamic that not only bolsters the town’s events and happenings but also helps the community thrive. A shining example of this communal harmony is the burgeoning relationship with Jimmy Hayden, whose contributions are instrumental in the expansion and success of the Leonardtown Summer Music Festival. This partnership exemplifies how local business leaders can play a pivotal role in cultivating cultural events that resonate with the community’s heart, thereby enhancing Leonardtown’s charm and vibrancy through shared experiences and celebrations.
The 2024 season of the Leonardtown Summer Music Festival is set to kick off this month with the return of the On the Waterโs Edge Concert Series at the Leonardtown Wharf. The series, a cornerstone of the festival, is poised to launch on April 20th with a spectacular concert by Trio Caliente from 5 p.m. to 7 p.m. Known for their electrifying blend of Flamenco, Pop, and Latin Dance Music, Trio Caliente is set to ignite the stage and set the tone for a summer filled with diverse musical experiences, offering a dynamic calendar of events throughout the entire season. The 2024 lineup features a variety of notable acts such as Cover Your Six, N2N Band, Six Gun South, and Copper Pennies, among others.
The Leonardtown Summer Music Festival has always been a beacon of vibrant celebration within the community. With the introduction of On the Waterโs Edge, the series has elevated the festival to new heights, transforming it into an exhilarating experience. This addition has infused the festival with fresh energy, marrying the tranquil beauty of waterside performances with the lively atmosphere of summer festivities. As attendees revel in the blend of scenic views and captivating music, the festival now offers a richer, more immersive journey through culture and melody, making each moment spent by the water’s edge memorable.

A Vision of Musical Diversity and Community Celebration
Behind this extraordinary celebration of music and community spirit is Jimmy Hayden, a name synonymous with local dedication and philanthropy. As a native of St. Maryโs County and a seasoned realtor with RE/MAX 100, Haydenโs deep roots in the community have blossomed into a mission to enrich his hometown through music and engagement.
The On the Waterโs Edge Concert Series, under Haydenโs sponsorship and visionary guidance, has been crafted to offer something for everyone. The concert series spans a range of themes, from Latin and R&B Nights to Teacher and Military Appreciation Days, ensuring that each event not only entertains but also resonates with the diverse community it serves. Hayden’s partnership with the town and the Leonardtown Business Association to host these events at the picturesque Leonardtown Wharf underscores a commitment to leveraging local beauty to enhance cultural offerings. Every month features a dynamic event, culminating in an exhilarating finale on August 31st from 5 p.m. to 8 p.m., with Southern rock bands Six Gun South and Copper Pennies. The evening will be topped off with a magnificent fireworks display, ensuring a memorable conclusion to this yearโs Wharf concert series (the music festival itself continues through October). True to the spirit of inclusivity and accessibility, the On the Waterโs Edge Series welcomes attendees from all walks of life. Whether arriving by boat to tie up at the Wharfโs slips or by land, possibly riding the free Leonardtown Trolley, the festival is a focal point of community engagement and celebration.
This season, the festival expands its reach with the introduction of Third Tuesday Tunes, an innovative series of concerts set to transform lunchtimes every third Tuesday from 12 p.m. – 1 p.m. This innovative series, also sponsored by Jimmy Hayden, will feature live music in Leonardtown Square that will be broadcast through the townโs sound system, offering a unique auditory experience. These Tuesday gatherings encourage the community to revel in a harmonious midday break, adding a new dimension to Leonardtown’s rich cultural fabric. Leonardtown’s Town Administrator, Laschelle McKay, shares insights into the depth of Hayden’s involvement, extending far beyond just sponsoring the โOn the Waterโs Edgeโ andโ Third Tuesday Tunesโ music series, โThe town and the Leonardtown Business Association have many partnerships which allows them to provide wonderful, family-friendly events for residents and visitors. For the last few years, one of those partners is Jimmy Hayden. Jimmy is not just the sponsor of the On the Waterโs Edge [and Third Tuesday Tunes] Concert Series, he works hard at every event to make sure the audience has a fun, quality experience and the community benefits in every way.โ

A Gold Star Example of Philanthropy and Community Service
Hayden’s impact on the community goes well beyond his involvement in the music festival. Through his real estate business, he actively participates in the Homes for Heroes program, which was initiated following the events of September 11. This program allows Hayden to donate 5% of his commission from the sale of a home directly to the “Hero” involved in the transactionโbe it military personnel, teachers, or first responders. The beneficiaries often use this contribution for home improvements, furnishings, and other needs. Since becoming a part of Homes for Heroes on December 13, 2018, Hayden has contributed roughly $150,000. His generosity places him third in the state and thirty-seventh nationally in terms of contributions made through the program. His dedication to service is also evident in his over thirty years as a volunteer firefighter with the Hollywood Fire Department, his role as Board Chair for both the St. Maryโs Chamber of Commerce and the Cedar Lane Senior Living Center, and his recent collaboration with the Blue Crabs Professional Baseball Club to honor local heroes.

Leonardtown’s Festival of Music and Community
At the heart of the Leonardtown Summer Music Festival is a symphony of support, vision, and community leadership embodied by Jimmy Hayden. His commitment to his hometown, love for music, and steadfast support for local heroes form the foundation of the festival. As the 2024 season gets underway, the united efforts of the Town of Leonardtown, the Leonardtown Business Association, and chief sponsor Jimmy Hayden aim to fill Leonardtown with music, bringing together families, friends, and neighbors.
This year’s Leonardtown Summer Music Festival continues to celebrate diversity, unity, and the joy of live music in the heart of the community. With a lineup that spans various genres and themes, it beckons people from all walks of life to join in, fostering a deep sense of belonging and community spirit. The excitement enveloping this year’s festival underscores a continuous commitment not just to sustain this vibrant celebration, but also to cultivate it into an esteemed annual tradition that profoundly enriches Leonardtown’s cultural scene and strengthens the bonds among its community members.
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To learn more about Jimmy Hayden, RE-MAX 100 and Homes for Heroes visit:
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