Events

Join us for an unforgettable afternoon with Ben Fisher, a solo acoustic performer from Frederick, Maryland. His sound brings together ’90s Country, Yacht Rock, and Folk, creating the perfect backdrop for great wine and good company.

David is a seasoned DC-area musician who has been performing since age nine. Known for his versatility, he blends influences from pop, rock, reggae, hip-hop, and indie, and has played everything from vocals and rhythm guitar to drums, bass, and keys. He’s currently working on his solo debut Doux-Amer with Nathon Haddon of Haddon Records and also founded the nostalgic alternative rock DJ series Back To The 90s.
David has shared the stage with artists like Weezer, Ryan Cabrera, Ash, Ballyhoo!, and Ozma, and has performed at major venues including Nationals Park, The Fillmore, Union Stage, and Jammin’ Java.
Come enjoy a great afternoon of live music with David at Fleetwood!

Join us for an incredible live performance with Shane Hines, a powerhouse singer-songwriter and producer whose music bridges pop, rock, country, and Americana. With years of experience writing and producing alongside top Nashville talent, Shane brings grit, honesty, and emotion to every song.
A John Lennon Songwriting Contest finalist and acclaimed performer, his sound blends heartfelt lyrics with polished musicianship. Get ready for an unforgettable afternoon of live music!

Join us for an afternoon of live music with Benjamin Weimer, a talented and down-to-earth performer bringing an incredible mix of rock, pop, and country classics to life. From timeless hits by Johnny Cash and Tom Petty to favorites by Green Day and Lynyrd Skynyrd, Benjamin’s versatile repertoire has something for everyone.
Grab a glass of wine, kick back, and enjoy an afternoon of great music in the relaxed ambiance of Fleetwood. Don’t miss it!

Spend your afternoon unwinding with Luke Andrews, whose versatile setlist offers a little something for everyone. Enjoy a blend of country, folk, indie, Americana, blues, jazz, and soft classic rock—all delivered with a cozy, coffeehouse vibe.
Pair the music with your favorite Fleetwood wine and make it a relaxing day to remember!

Enjoy an unforgettable afternoon of live music at Fleetwood Farm Winery with Rook Richards! Blending country, pop, ‘90s alternative, and acoustic rock, Rook brings a uniquely soulful sound defined by ethereal vocals and heartfelt, story-driven lyrics. His acoustic performance style creates an intimate, easygoing atmosphere, perfect for relaxing with a glass of wine and taking in the vineyard views!

Join us for an afternoon of music with Shane Gamble, a Maryland native blending Country, Rock, Pop, and Americana into a sound that’s uniquely his own. With a career that includes a Top 10 single on SiriusXM’s The Highway and his acclaimed album American Heart, Shane’s music captures the essence of heartfelt storytelling and raw energy.
Often compared to legends like Tom Petty and Bruce Springsteen with a modern twist, Shane’s performance is sure to leave an impression. Don’t miss this chance to experience his soulful voice and passionate guitar in the intimate setting of Fleetwood!

Grayson Moon, a talented singer-songwriter blending soulful vocals with contemporary guitar and electronic vibes. Drawing inspiration from legends like Sam Cooke and Elvis Presley, Grayson creates a unique Indie-Soul experience that’s sure to captivate.
With a background in classical voice and a passion for genre-blending soundscapes, Grayson has become a crowd favorite on stages across the East Coast. Don’t miss this opportunity to enjoy his soulful artistry in Fleetwood’s enchanting setting!