Live Music

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.

Scott Kurt brings a unique blend of Southern grit and Rust Belt rock to his signature country sound. Influenced by artists like Eric Church, Jon Pardi, Luke Combs, and Tom Petty, he delivers authentic, guitar-driven performances rooted in strong storytelling—evident in his single “American Man,” which reached the iTunes Country Top 40. His hard work and talent have earned him opening slots for major country acts including Cole Swindell, Montgomery Gentry, Jimmie Allen, Eli Young Band, Kip Moore, and Easton Corbin. Scott’s powerful mix of country and rock is the perfect fit for a great day at Fleetwood!

Join us for an unforgettable afternoon with Laura Cashman, a powerhouse vocalist and Best of Loudoun 2024 Finalist! Known for her unmatched energy and crowd engagement, Laura brings a wide-ranging setlist of hits from the 70s to today, along with a few original songs.
With her dynamic performances and acoustic guitar, Laura creates a fun, entertaining, and memorable experience. Don’t miss the chance to enjoy her incredible talent while sipping your favorite Fleetwood wines!

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!