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Labor Day Festival
Mon, Sep 7, 2026
12:00 PM – 5:00 PM
Labor Day at Keswick Vineyards! Join us Monday 12–5pm for a fun-filled Labor Day celebration with live music and wine.
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Live Music at Charlottesville-Area Wineries & Breweries
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.
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Labor Day Music with Smokin' Trout plus Grill & Chill
Mon, Sep 7, 2026
2:00 PM – 5:00 PM
Celtic, Americana, folk, bluegrass, rock, blues from Smokin' Trout. Plus Grill & Chill on Labor Day.
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Live Music: Jon Spear
Mon, Sep 7, 2026
2:30 PM – 4:30 PM
Jon Spear is a Charlottesville-area favorite whose music moves between genres. Labor Day Monday 2:30-4:30PM at Albemarle CiderWorks.
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C-VILLE Chamber Music Festival: Pastoral Landscapes
Wed, Sep 9, 2026
6:00 PM – 9:00 PM
C-VILLE Chamber Music Festival at Hazy Mountain, featuring Colin Jacobsen and Beethoven's Pastoral Symphony arr. for flute and strings. Doors open 6PM, music starts 7:30PM. Tickets required.
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Porch Nights: Michael Clem
Thu, Sep 10, 2026
5:00 PM – 8:00 PM
Porch Nights at Eastwood with Michael Clem. Outdoor live music, no reservations, no cover.
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Friday Sundowner's Music Series featuring Bailey Hayes
Fri, Sep 11, 2026
5:00 PM – 9:00 PM
The Friday Sundowner's Music Series at Merrie Mill Farm & Vineyard, featuring Bailey Hayes.
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Live Music: Jon Spear Band
Fri, Sep 11, 2026
5:00 PM
Charlottesville blues band formed in 2012.
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Friday Night Out with John Kelly & Half Price Wine Flights
Fri, Sep 11, 2026
5:00 PM – 8:00 PM
Long-time local musician John Kelly with half-price wine flights.
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Virginia Oyster & Wine with Live Music: John Kelly
Fri, Sep 11, 2026
5:00 PM – 8:00 PM
Virginia oysters and wine every Friday. Live music by John Kelly 5-8PM. No reservations needed.
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The Jen Tal Band Live
Fri, Sep 11, 2026
5:30 PM
Soulful original music and classic covers by The Jen Tal Band at Potter's Craft Cider.
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ian. (Ian Gilliam & The FireKings)
Fri, Sep 11, 2026
6:00 PM
Blues, Rockabilly, Honky Tonk, and Rock & Roll music live at Glass House.
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Blair's West Live Music
Fri, Sep 11, 2026
7:00 PM
Live music at Pro Re Nata Brewpub & Music Hall in Crozet. Mountain views, craft beer, and great live music.
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Live Music | Josh Davidson
Sat, Sep 12, 2026
12:00 PM – 4:00 PM
Josh Davidson plays a wide variety of music, hailing from the Blue Ridge Mountains of Virginia.
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Live Music: Brian Franke
Sat, Sep 12, 2026
12:30 PM – 3:30 PM
Live music from Brian Franke 12:30-3:30PM during Oktoberfest at Eastwood.
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John Kelly Live Music
Sat, Sep 12, 2026
2:00 PM
John Kelly is a Charlottesville-based singer-songwriter with more than two decades of solo acoustic performing experience, now a regular on the Central Virginia singer-songwriter circuit.
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Second Saturday Music with Mike Proffitt
Sat, Sep 12, 2026
2:00 PM – 5:00 PM
Live music in the mountains with Mike Proffitt.
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Live Music: John Shenk
Sat, Sep 12, 2026
3:00 PM
Central-Virginia singer-songwriter blending rock, bluegrass, folk, and blues.
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Jay Pun & Jen Tal Live at Blenheim
Sat, Sep 12, 2026
3:00 PM – 5:00 PM
Free live music at Blenheim Vineyards under the tent overlooking the vineyard, featuring Jay Pun & Jen Tal and their Afro Soul sound.
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Sweet Jane's Kitchen & Midnight Buzz Band
Sat, Sep 12, 2026
4:00 PM – 7:00 PM
Sweet Jane's Kitchen food truck and live music by the Midnight Buzz Band at Hark Vineyards.
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Live Music: The Zip
Sat, Sep 12, 2026
4:00 PM – 7:00 PM
Live music at Afton Mountain Vineyards featuring The Zip. Tasting Room Open 11am-7:30pm.
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Eastwood After Dark: Lockjaw Classic Rock
Sat, Sep 12, 2026
5:00 PM – 8:00 PM
Eastwood After Dark - Lockjaw Classic Rock 5-8PM. Live music and dancing every Saturday night.
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Second Saturday Music by Scuffletown
Sat, Sep 12, 2026
6:00 PM – 9:00 PM
Live music in the mountains by Scuffletown.
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The Unsuitables
Sat, Sep 12, 2026
6:00 PM – 9:00 PM
Into classic rock like the Stones and the Kinks? This beloved local band brings the excitement every time.
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Cumberland Road Live Music
Sat, Sep 12, 2026
7:00 PM
Live music at Pro Re Nata Brewpub & Music Hall in Crozet. Mountain views, craft beer, and great live music.
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Live Music with Pat Anderson
Sun, Sep 13, 2026
12:00 PM – 4:00 PM
Oklahoma-born and Virginia-raised, Pat Anderson is a soloist who pours his heart into every performance.
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Music on the Deck: Don Hancock
Sun, Sep 13, 2026
2:00 PM – 5:00 PM
Join us for music on the deck from 2-5pm with Don Hancock at Cardinal Point Winery.
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Live Music: Andy Tichenor
Sun, Sep 13, 2026
2:00 PM
Jam-band heart with warm vocals and Grateful Dead-inspired improvisation.
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Sharif Music
Sun, Sep 13, 2026
2:00 PM – 5:00 PM
Live music with Sharif at Hark Vineyards.
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Cider & Strings: An Afternoon w/ Mighty Fine Company Live
Sun, Sep 13, 2026
2:00 PM
Sunday afternoons are better with live music — Cider & Strings with Mighty Fine Company at Potter's Craft Cider.
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Thomas Gunn Live
Sun, Sep 13, 2026
2:00 PM
Thomas Gunn performing live. Regular player with The Pollocks and Michael Clem.
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Live Music: Ellen Ruth
Sun, Sep 13, 2026
3:00 PM – 5:00 PM
Live music by Ellen Ruth at Starr Hill Brewery Crozet.
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Max Mandu Live Music
Wed, Sep 16, 2026
12:00 PM – 3:00 PM
Live music at Pippin Hill Farm & Vineyards featuring Max Mandu. 12pm-3pm.
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Wine Down Wednesday with The Unsuitables
Wed, Sep 16, 2026
5:30 PM – 8:30 PM
A night of fantastic music featuring Motown, classic rock, and more covers with The Unsuitables.
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The Front Porch Presents: Jake Blount Band
Wed, Sep 16, 2026
5:30 PM
Jake Blount Band at Potter's Craft Cider, presented by The Front Porch. Grab your tickets!
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Porch Nights: Jim Richardson
Thu, Sep 17, 2026
5:00 PM – 8:00 PM
Porch Nights at Eastwood with Jim Richardson. Outdoor live music on the veranda. No reservations, no cover.
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The Front Porch Presents: Songwriter's Open Mic
Thu, Sep 17, 2026
7:00 PM
Calling all songwriters! The Front Porch presents Songwriter's Open Mic at Potter's Craft Cider.
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Virginia Oyster & Wine with Live Music: Matthew O'Donnell
Fri, Sep 18, 2026
5:00 PM – 8:00 PM
Virginia oysters and wine every Friday. Live music by Matthew O'Donnell 5-8PM. No reservations needed.
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Friday Night Out with Bomar & Ritter & Half Price Wine Flights
Fri, Sep 18, 2026
5:00 PM – 8:00 PM
Live music by Bomar & Ritter with half-price wine flights.
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Live Music: Bluzonia
Fri, Sep 18, 2026
5:00 PM
Four-piece band featuring the drummer from the Jon Spear Band.
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Friday Sundowner's Music Series featuring Mercy Creek
Fri, Sep 18, 2026
5:30 PM – 8:30 PM
The Friday Sundowner's Music Series at Merrie Mill Farm & Vineyard, featuring Mercy Creek.
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Tara Mills Band Live
Fri, Sep 18, 2026
5:30 PM
A blend of folk, bluegrass, and Americana by the Tara Mills Band at Potter's Craft Cider.
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Ken Farmer & The Authenticators
Fri, Sep 18, 2026
6:00 PM – 8:30 PM
Rocking good fun with Ken Farmer & The Authenticators. Open to all, no cover.
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Live Music – Rixeyville Revival
Sat, Sep 19, 2026
12:00 PM – 4:00 PM
Come out and rock with the Rixeyville Revival Band — bringing the best hits from the rock era.
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Live Music: Heidi Riddell
Sat, Sep 19, 2026
12:30 PM – 3:30 PM
Live music from Heidi Riddell 12:30-3:30PM during Eastwood's Oktoberfest weekend.
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Music in the Mountains with Kat and the Travelers
Sat, Sep 19, 2026
2:00 PM – 5:00 PM
Live music in the mountains with Kat and the Travelers.
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Oktoberfest with Guten Morgen Band
Sat, Sep 19, 2026
2:00 PM
Celebrate Oktoberfest! The Guten Morgen Band from Staunton plays German, Austrian, and Central European waltzes and polkas on accordion and bass. German foods from Chef Roderick and lots of beer!
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Live Music: Andrew Beverly
Sat, Sep 19, 2026
3:00 PM
Live music in the beer garden at Brewing Tree.
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Tucker Wyatt Live at Blenheim
Sat, Sep 19, 2026
3:00 PM – 5:00 PM
Free live music with Tucker Wyatt at Blenheim Vineyards under the tent overlooking the vineyard. Grab a glass of Blenheim wine and enjoy an easy fall afternoon.
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Pat Anderson Music
Sun, Sep 6, 2026
3:00 PM – 6:00 PM
Live music with Pat Anderson at Hark Vineyards.
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Music on the Deck: Transatlantic Invasion
Sun, Sep 6, 2026
2:00 PM – 5:00 PM
Join us for music on the deck from 2-5pm with Transatlantic Invasion at Cardinal Point Winery.
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Long Live the Jam!
Sun, Sep 6, 2026
2:00 PM – 5:00 PM
Open jam session at Starr Hill Brewery Crozet. Bring your instrument or just come listen and enjoy great beer.
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Live Music: Tony Hirtz
Sun, Sep 6, 2026
2:00 PM
Live music in the beer garden at Brewing Tree.
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MusicPast
Music In The Mountains with Tropical Attitudes: Jimmy Buffet Tribute
Sun, Sep 6, 2026
2:00 PM – 5:00 PM
Honoring Jimmy Buffet on the anniversary of his death. Cool wines, mountain streams, shaded patios, and amazing music.
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Rusty Speidel and Tom Goodrich
Sun, Sep 6, 2026
2:00 PM
Rock and Americana from the duo that makes up half of SGGL. Sunday Fun Day.
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