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.

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!

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!

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!