• Ryan Sill

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Lindsay Austin Duo

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Ryan Sill

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • David Goodrum

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Luke Andrews

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Grayson Moon

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Shane Gamble Duo

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Chris Compton

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    Chris Compton is a talented singer-songwriter and multi-instrumentalist based in the VA/MD/DC area, recognized for his soulful vocals, acoustic guitar talent, and dynamic live performances. Blending pop, rock, and country influences, Chris creates an engaging atmosphere that connects with audiences of all kinds. We’re excited to welcome Chris Compton to Fleetwood and can’t wait for guests to enjoy his versatile sound and live music experience!

  • Ryan Sill

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Grayson Moon

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Ryan Sill

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!

  • Benjamin Weimer

    Fleetwood Farm Winery 23075 Evergreen Mills Rd., Leesburg, VA, United States

    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!