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!

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!

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!

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!

Join us for an afternoon of music with Dave Goodrum, a Leesburg-based solo acoustic artist performing hits from the ’70s to today.
Blending rock, blues, funk, pop, and more, Dave brings a fresh mix of favorites from John Mayer to Johnny Cash, plus creative mashups and deep cuts that keep every set unique. You won’t want to miss this great live performance!