
Wine Down Wednesday – The Unsuitables
Join us for a night of fantastic music featuring a variety of covers, including Motown, classic rock, and more with The Unsuitables.
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Live music is the heartbeat of Charlottesville wine country — nearly every winery, brewery, and cidery hosts local bands on weekends. Find every show on one calendar, from Friday-night patio sets to Sunday-afternoon lawn concerts.

Join us for a night of fantastic music featuring a variety of covers, including Motown, classic rock, and more with The Unsuitables.
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Porch Nights live music series at Eastwood Farm and Winery featuring Jim Richardson.
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Tailgate Thursdays continue! Thursday, July 16th (6–9 PM). Live Music: Susie + The Pistols. Fresh Eats: Oyster Catcher Sea Farms will be on-site with fresh and grilled oysters on the half shell. The grills are fired up and ready for you!
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Live music at Eastwood Farm and Winery featuring Sue Harlow.
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Live music at Jefferson Vineyards featuring Melissa Hansen. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, July 17, 5–7pm.
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Join us every Friday night for live music 5:30-8 and fried seafood specials!
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Friday Sundowner's Music Series at Merrie Mill Farm & Vineyard, featuring Blane Perry and Bob Ledbetter. Music 5:30-8:30pm.
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A priceless night of rocking good fun featuring KEN FARMER & THE AUTHENTICATORS! From 6 to 8:30pm. Brick City Kitchen Food Truck will be on site. Open to all. No cover.
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Live music by Chickenhead Blues paired with Oyster Catcher Sea Farms at Chisholm Vineyards' Friday Sunset Soirée series.
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Live music at Eastwood Farm and Winery featuring FarAway.
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Big Gavel Country Band blends classic Americana acoustic with added percussion, creating a rhythmic and dynamic sound. Saturday afternoon performance at Keswick Vineyards.
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Come join us, grab a glass of cider and a warm reception from Tara Mills! Inspired by the Blue Ridge Mountains.
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Live music at Afton Mountain Vineyards. Food truck on site. Tasting Room Open 11-7:30PM.
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Bunch O' Mugs makes their official debut at Glass House Winery & Brewery! This brand new musical blend has been percolating and is ready to be savored. Open to all.
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Eastwood After Dark - Live Music & Dancing Every Saturday Night featuring The Wavelength.
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Live music at Eastwood Farm and Winery featuring Ty Burkhardt.
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Laid-back Sunday afternoon live music session featuring The Trio at Chisholm Vineyards.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Paxton Henderson. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, July 19, 2–4pm.
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A fantastic Sunday Funday with music by the Midnight Buzz Duo, featuring the talented husband-and-wife team Tracey and Barry Collins. They deliver a special acoustic performance filled with classic rock favorites. Open to all.
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Enjoy Wednesday evening with Keswick wines, local beers, or canned cocktails. South Canal Street brings an eclectic mix of music to the courtyard.
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Porch Nights live music series at Eastwood Farm and Winery featuring Anthony Semiao.
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Tailgate Thursdays continue! Thursday, July 23rd (6–9 PM). Live Music: Moonglow. Fresh Eats: Crozet Seafood will be on-site. The grills are fired up and ready for you! Pack your dancing shoes, favorite grill-ables, lawn games, and picnic blankets.
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Supernova isn't just another tribute band — this six-piece outfit is obsessed with recreating the energy, intensity, and swagger of a live Oasis performance. Free admission.
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Enjoy great wine along with great music from Gina Sobel and Matt Draper.
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Live music at Eastwood Farm and Winery featuring Jamal Millner Trio.
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Live music at Jefferson Vineyards featuring Chris Hammock. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, July 24, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Join us every Friday for live, local music from 5:30-8 with no cover charge!
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Live music by Scuffletown paired with Twisted Provisions food at Chisholm Vineyards' Friday Sunset Soirée series.
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The Gladstones return to the tropical oasis at Glass House Winery in Free Union! Get ready to rock out to their great rock 'n' roll and original tunes. Open to all.
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Danny Jams is an indie-electronic loop artist based in Richmond, VA. His music combines jam-focused improvisations with electronic elements.
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Live music at Eastwood Farm and Winery featuring Paxton Henderson.
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There is no better way to spend a Saturday afternoon than at Valley Road Vineyards + the engaging performance of Shane Click! Don't miss it!
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Join Woodbrook Farm Vineyard for a perfect Saturday afternoon with live music by Cason Spencer and a visit from Cousin's Maine Lobster food truck, set against the beautiful Blue Ridge Mountains.
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Live music at Afton Mountain Vineyards. Food truck on site. Tasting Room Open 11-7:30PM.
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Eastwood After Dark - Live Music & Dancing Every Saturday Night featuring Eli Cook Band.
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The Charlottesville Blues Revue comes to Glass House Winery! This mega-talented lineup features area favorites who have performed on the GHW stage before, but never all together at the same time. Come early! Open to all.
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Collecting inspiration from many different sources, Andy Tichenor pieces them together to create an eclectic mix of music. Sunday afternoon performance at Keswick Vineyards.
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Laid-back Sunday afternoon live music session featuring The Michael Elswick Gathering at Chisholm Vineyards.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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An incredible musical treat featuring fantastic singer/songwriter John Kelly on guitar and vocals joined by the magnificent harmonica wizard Gary Green. From 2 to 5pm. Open to all. No cover.
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Live music at Jefferson Vineyards featuring Gina Sobel. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, July 26, 2–4pm.
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Scuffletown brings a unique blend of originals, roots, and high-energy music to Keswick Vineyards! Come enjoy wine and great music on a Wednesday evening.
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Porch Nights live music series at Eastwood Farm and Winery featuring Ron Gentry.
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Tailgate Thursdays continue! Thursday, July 30th (6–9 PM). Live Music: Scuffletown. Fresh Eats: Oyster Catcher Sea Farms will be on-site with fresh and grilled oysters on the half shell. The grills are fired up and ready for you!
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2026 Summer Concert Series at Trump Cidery featuring Lama & The Hound: 4-7pm. Enjoy an unforgettable season of live music at Trump Cidery, located at 3550 Blenheim Road. Sip estate-crafted cider, take in vineyard views, and unwind with friends. Admission is complimentary.
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Live music at Jefferson Vineyards featuring Sean Patrick. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, July 31, 5–7pm.
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Live music at Eastwood Farm and Winery featuring Eli Cook.
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Final Fridays Concert at Pollak Vineyards featuring Blake Hunter & the Gatherers. Food truck: Crozet Seafood Supply. Live music under the Blue Ridge skies.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Join us every Friday for live, local music from 5:30-8:30 with no cover charge!
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Live music by Little Walter & the Convictions paired with Sweet Jane's Kitchen at Chisholm Vineyards' Friday Sunset Soirée series.
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DON'T LOOK UP features Andy Burdetsky (bass/vocals), Dave Sherman (guitar/vocals), Rob Martin (guitar/vocals), and Lance Foster (drums/vocals) performing Americana music that's deeply rooted in the Blues. Open to all.
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Shotguns N Roses pride themselves on being the most accurate and faithful Guns N' Roses experience you can get! With a powerful frontman and a ferocious band, they bring all the classic outfits, instruments and stage props from GNR 1987–1993. GA tickets $20 presale / $25 door. VIP Tables available (21+).
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The Voice legend and local favorite Matt Johnson! Come grab a glass or bottle of your favorite Keswick wine and enjoy an afternoon of great music.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Laid-back Sunday afternoon live music session featuring Jacob Paul Allen at Chisholm Vineyards.
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Live music at Jefferson Vineyards featuring Mojo Pie. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, August 2, 2–4pm.
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Join us for Field Day at Blenheim Vineyards and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. Susie & The Pistols will be playing live from 3-5 PM under the tent overlooking the vineyard. Bring the whole family, invite your friends, and settle in for an afternoon of great wine.
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Live music at Jefferson Vineyards featuring Nicholas Darden. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, August 7, 5–7pm.
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Please help us welcome Travis Elliott back to Valley Road Vineyards for this Late Friday appearance. A Charlottesville, Virginia-based singer, songwriter, and guitarist with roots in Richmond, his sound blends alternative pop hooks, punk energy, and Americana grit, earning praise as a "modern rock epic."
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:00-9:00pm.
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Live music by Brandon Wayne and His Lonesome Drifters paired with Oyster Catcher Sea Farms at Chisholm Vineyards' Friday Sunset Soirée series.
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Laid-back Sunday afternoon live music session featuring Dave's Basement at Chisholm Vineyards.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Gina Sobel. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, August 9, 2–4pm.
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Relatively new to the live music scene, Tristan recently moved to Nelson County and has been playing at Basic Necessities on Sunday mornings. He's delighted to be back at Valley Road for an encore performance.
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Live music at Jefferson Vineyards featuring Gina Sobel. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, August 14, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music by The Inclinators paired with Crozet Seafood Supply at Chisholm Vineyards' Friday Sunset Soirée series.
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A triple-bill featuring guitarist Isaac Hadden, John Daniel Ray (progressive jazz bassist and composer), and legendary fusion drummer Jeff Sipe. An evening of exploratory improvised music.
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Blasting out of the Tri-State area (NY, NJ, PA), Obey Your Master performs a full catalog of Metallica hits from Kill 'Em All to 72 Seasons. The most authentic, face-melting Metallica tribute show around.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Laid-back Sunday afternoon live music session featuring The Trio at Chisholm Vineyards.
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Live music at Jefferson Vineyards featuring Paxton Henderson. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, August 16, 2–4pm.
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Live music at Jefferson Vineyards featuring Bob & Kenn. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, August 21, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music by Chickenhead Blues paired with Arepas on Wheels food truck at Chisholm Vineyards' Thursday Sunset Soirée series.
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Starry Nights returns to Veritas Vineyards & Winery for one night only! Relax under the stars as you drink your favorite wines and dance the night away to music from Hipshack. Bring a picnic and lawn chairs, or enjoy a stationed or plated meal prepared by the chefs.
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Saturday evening live music featuring The Shacktones at Chisholm Vineyards.
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Laid-back Sunday afternoon live music session featuring The Michael Elswick Gathering at Chisholm Vineyards.
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Live music at Jefferson Vineyards featuring Jerry Cappa. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, August 23, 2–4pm.
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Live music at Jefferson Vineyards featuring Chris Hammock. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, August 28, 5–7pm.
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Don't miss VRV favorite, Ron Gentry. A great way to celebrate a Friday night. Ron's music is a delight and is always the perfect accompaniment to Valley Road wine!
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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A throwback DJ night featuring 70's and 80's hits by Signature DJ, paired with Twisted Provisions food at Chisholm Vineyards.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Joel Streeter. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, August 30, 2–4pm.
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Live music at Jefferson Vineyards featuring Melissa Hansen. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, September 4, 5–7pm.
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Sundowner's Music Series at Merrie Mill Farm & Vineyard featuring Disco Risque Solo. Music 1:00-4:00pm.
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Join us for Field Day at Blenheim Vineyards and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. The Norms will be playing live from 3-5 PM under the tent overlooking the vineyard.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Her Checkered Past. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, September 6, 2–4pm.
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Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, September 7, 2026.
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Sue Harlow is an Americana-Folk Singer/Songwriter whose haunting vocals delve into the depths of what makes people real.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:00-9:00pm.
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Live music at Jefferson Vineyards featuring Sue Harlow. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, September 11, 5–7pm.
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Dave Goodrich brings his eclectic array of songs and musical styles to Valley Road for an afternoon of music you won't want to miss!
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Live music at Jefferson Vineyards featuring Chris Hammock. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, September 13, 2–4pm.
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Live music at Jefferson Vineyards featuring Melissa Hansen. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, September 18, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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DMTB is a celebration of the music of the Dave Matthews Band — a time machine to the 90s with complex guitar riffs, soaring violin melodies, smooth sax lines, and explosive drumming. Buffalo, NY based band with 2000+ shows in 46 states and 10 countries.
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The tight harmonies of FarAway return to Valley Road Vineyards for an afternoon of music and wine. So grab your friends and a bottle of wine – this is one you won't want to miss!
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Paxton Henderson. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, September 20, 2–4pm.
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Live music at Jefferson Vineyards featuring Kevin McMahon. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, September 25, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music at Jefferson Vineyards featuring Matty & Mirabelle. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, September 27, 2–4pm.
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Join us for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music at Jefferson Vineyards featuring Joel Streeter. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, October 2, 5–7pm.
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It's our last Late Friday AND it's the beginning of Virginia Wine Month. So come stay late, enjoy a glass or bottle of wine, and enjoy great tunes from Ron Gentry.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Set sail on a groovy voyage through the smooth sounds of the 70s and 80s! Thurston Howell crafts a symphony of classic hits from Toto, Michael McDonald, Hall & Oates, and Steely Dan. Because You Can't Fake SMOOTH!
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Join us for Field Day at Blenheim Vineyards presented by WNRN radio, and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. Small Town Rodeo will be playing live from 3-5 PM under the tent overlooking the vineyard.
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Full Moon Fever is back for an epic Tom Petty party celebrating the birthday of Tom Petty and the 50th anniversary of American Girl! Performing all your favorite Petty hits with high-energy authenticity.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Melissa Hansen. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, October 4, 2–4pm.
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Live music at Jefferson Vineyards featuring Sean Patrick. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, October 9, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music at Jefferson Vineyards featuring Jerry Cappa. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, October 11, 2–4pm.
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Live music at Jefferson Vineyards featuring Chris Hammock. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, October 16, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:00-9:00pm.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Joel Streeter. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, October 18, 2–4pm.
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Live music at Jefferson Vineyards featuring Sue Harlow. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, October 23, 5–7pm.
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Join us every Friday for the Sundowner's Music Series at Merrie Mill Farm & Vineyard. Music 5:30-8:30pm.
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Live music at Jefferson Vineyards featuring Matty & Mirabelle. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. October 24, 2–4pm.
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Join us for the last Sunday Jazz and Blues of the season at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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Live music at Jefferson Vineyards featuring Bob & Kenn. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, October 30, 5–7pm.
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Join us for the last Friday Sundowner's of the season at Merrie Mill Farm & Vineyard featuring Wavelength. Music 5:30-8:30pm.
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Live music at Jefferson Vineyards featuring Chris Hammock. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, November 1, 2–4pm.
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Live music at Jefferson Vineyards featuring Gina Sobel. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, November 6, 5–7pm.
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Live music at Jefferson Vineyards featuring Melissa Hansen. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, November 8, 2–4pm.
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Live music at Jefferson Vineyards featuring Paxton Henderson. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Friday, November 13, 5–7pm.
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Pandora's Box Tribute has been rocking stages across the US and internationally since 2015. They'll take you on a high-octane journey through 50 years of mega hits from one of the world's most iconic rock bands.
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Live music at Jefferson Vineyards featuring Matty & Mirabelle. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, November 15, 2–4pm.
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Black Friday music event at Merrie Mill Farm & Vineyard featuring Wavelength. Music 1:00-4:00pm.
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Enjoy this energetic and eclectic Irish jam session every 2nd Sunday of the month. Patrick & friends bring the best of Irish traditional music.
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Live music at Jefferson Vineyards featuring Matty & Mirabelle. Enjoy estate-grown wine while listening to live music nestled among the rolling hills and sun-drenched vines. Sunday, July 12, 2–4pm.
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Join us for music, mountain views, and wonderful wine. Dave Goodrich entertains with his rock-based repertoire including flavors of blues, rock, pop, Motown, and original music. He'll make you laugh and touch your heart with his soulful music.
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A super cool Sunday Funday with music by the Tara Mills Band. Tara Mills leads the band featuring guitar, banjo, bass, and mandolin performing an original blend of folk, bluegrass, and Americana. Open to all. No cover.
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Sunday live music featuring the Robert Jospé Quartet at Chisholm Vineyards' Sunset Soirée series.
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Join us every Sunday for Jazz and Blues at Merrie Mill Farm & Vineyard. Music 1:00-4:00pm.
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