Events

Karen Jonas is an acclaimed singer-songwriter and poet known for her cinematic, whiskey-soaked Americana sound and razor-sharp, emotionally honest storytelling. Blending indie noir with roots music, her songs and poems […]

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!

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 with Ryan Sill, a talented singer-songwriter and finalist from The Voice Season 7. Known for his smooth pop vocals blended with the soulful edge of blues and rock, Ryan brings a captivating performance to every stage.
Currently producing his debut album, Ryan’s music is available on all streaming platforms. Don’t miss the chance to enjoy his incredible sound while sipping your favorite Fleetwood wines!

Join us for an afternoon with Gary Smallwood, a seasoned musician whose soulful, guitar-driven sound blends classic rock, blues, country, and funk. Performing professionally since age 16,
Gary has shared the stage with legendary acts like Robin Trower, The Marshall Tucker Band, and Bret Michaels. With over 200 shows a year, his passion and talent shine through every performance, bringing decades of experience and a love for all styles of music to the stage. Don’t miss this incredible live show!

Dan McGuire is a talented guitarist, singer, and bandleader based in the Frederick, Maryland area, known for delivering engaging live performances at weddings, wineries, and corporate events throughout Virginia, Washington D.C., and Maryland. Whether performing solo acoustic sets or with the Dan McGuire Group, he brings an energetic mix of music spanning multiple decades and genres, creating the perfect atmosphere for any occasion. We’re excited to welcome Dan McGuire to Fleetwood and look forward to sharing his incredible live music with our guests!

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!

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.