Events

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 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!

Spend your afternoon with the Lindsay Austin Duo, bringing their signature blend of acoustic charm and smooth harmonies to Fleetwood. Perfect for a laid-back day with great wine, their performance offers an enjoyable mix of songs to set the mood.
Relax, unwind, and let their music be the perfect backdrop to your weekend!

Zach Jones is a Northern Virginia–based musician known for his versatile solo acoustic sets. His performances blend classics and modern favorites—from The Beatles and Neil Young to John Mayer, Dave Matthews Band, The Black Keys, Noah Kahan, and more—plus a few original songs.
A regular performer at local breweries, wineries, and private events, Zach brings an engaging acoustic sound wherever he plays. We’re excited to welcome him to 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!

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!