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42 events · This Weekend · Fri, Oct 23 – Sun, Oct 25
Miles Pearce Duo at Fallen Tree Vineyard
Music

Miles Pearce Duo

Fri, Oct 23, 2026
4:30 PM – 7:30 PM

The Miles Pearce Duo brings a lively mix of jazz, folk, Americana and Latin rhythms to the Charlottesville music scene. Grab a glass and settle in for an evening of acoustic music with a little flavor from around the world.

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Friday Night Out with Mirabelle & Matty at Ducard
Music

Friday Night Out with Mirabelle & Matty

Fri, Oct 23, 2026
5:00 PM – 8:00 PM

Join us for the first Friday Night Out with music by Mirabelle & Matty. This amazing duo will entertain you with fabulous and fun sing-along tunes. Wine flights are half price after 4 pm. Bring your own picnic or select from our lite noshing menu. Warm up the pipes and enjoy some DuCard wine as you enjoy the rhythm & views! No cover. Reservations are recommended. Make yours here today.

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Chickenhead Blues Band with Canelos Burritos at Glass House
Music

Chickenhead Blues Band with Canelos Burritos

Fri, Oct 23, 2026
6:00 PM – 8:30 PM

Kick off the weekend with the "New Orleans boogie-woogie, upbeat, rhythm and blues" sounds of the Chickenhead Blues Band, performing live inside the glass house conservatory. Friday, October 23rd, 6 to 8:30pm. No cover. Open to all. Band: Aric van Brocklin – Guitar, Skip Haga – Keyboards, Jeff Louderback – Drums, Jack Sheehan – Sax, Vic Brown – Bass. Canelos Burritos food truck will be onsite with service beginning at 5:30pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

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The Four Horsemen & Vulgar Display of Pantera at Basic City Beer Co.
Music

The Four Horsemen & Vulgar Display of Pantera

Fri, Oct 23, 2026
8:00 PM – 11:59 PM

THE FOUR HORSEMEN ARE COMING BACK TO THE FOUNDRY — AND THIS TIME, THEY’RE BRINGING VULGAR DISPLAY OF PANTERA WITH THEM. Friday, October 23rd, we’re turning The Foundry over to the music of two absolute giants of metal. THE FOUR HORSEMEN – A Celebration of Metallica with VULGAR DISPLAY OF PANTERA – A Tribute to Pantera The Four Horsemen have built a reputation as one of the country’s premier celebrations of Metallica, bringing the sound, precision, energy, and sheer force of a Metallica show to the stage. Now throw Vulgar Display of Pantera into the mix. Two legendary catalogs. Two full-throttle tributes. One massive night of metal in Waynesboro. Friday, October 23rd, 2026 The Foundry at Basic City Beer Co. Waynesboro, Virginia Genre: Heavy Metal Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

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Live Music | Danny Jams at Keswick Vineyards
Music

Live Music | Danny Jams

Sat, Oct 24, 2026
12:00 PM – 4:00 PM

Danny Jams is an indie-electronic loop artist based in Richmond, VA. His music combines jam focused guitar performances over electro-funk rhythms that weave together both songwriting & improv. Gaining inspiration from Grateful Dead & Phish, Danny keeps every show different and turns every song into a Jam.

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Music in the Mountains with Jimmy O at Ducard
Music

Music in the Mountains with Jimmy O

Sat, Oct 24, 2026
2:00 PM – 5:00 PM

Spend a beautiful afternoon relaxing at the winery and listening to the music of Jimmy O. He is an amazing guitarist with an unique style of classic rock, oldies, and a rockin’ country mix that’s sure to please everyone! Just add a bottle of wine, some great Virginia views, and you’ve set your weekend off to a great start! A lite noshing menu is available to accompany your wine. No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

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Five Old Gentlemen (FOG) Live at Blenheim Vineyards
Music

Five Old Gentlemen (FOG) Live

Sat, Oct 24, 2026
3:00 PM – 5:00 PM

Join us at Blenheim Vineyards on Saturday, October 24 from 3–5 PM for an afternoon of free live music with Five Old Gentlemen (FOG), a classic rock band covering tunes from the '50s to the '90s. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and enjoy a fall afternoon of live music, good company, and vineyard views. Free admission | No reservations required

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Classic Road 🎺 | Eastwood After Dark at Eastwood Farm and Winery
Music

Classic Road 🎺 | Eastwood After Dark

Sat, Oct 24, 2026
5:00 PM – 8:00 PM

Come see Classic Road! They will be playing from 5-8PM. Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.

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Mojo Parker Express at Bald Top Brewing Co.
Music

Mojo Parker Express

Sat, Oct 24, 2026
6:00 PM – 9:00 PM

Live music 6-9 PM. Mojo Parker is back! Their unique blend of soul, rock, funk and blues is well known throughout the valley and beyond - one of the area's most talented and dynamic groups.

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Glam'r Kiti Live at Basic City Beer Co.
Music

Glam'r Kiti Live

Sat, Oct 24, 2026
8:00 PM – 11:00 PM

GLAM'R KITI LIVE AT THE FOUNDRY — FREE SHOW Get ready for a night of big riffs, big hair, and straight-up rock & roll as Glam'r Kiti takes over The Foundry at Basic City Beer Co. on Saturday, October 24th! Best part? This one is FREE. No ticket required. Just show up, grab a drink, find your spot, and get ready to rock. Doors: 6:30 PM | Show: 8:00 PM FREE SHOW | ALL AGES — Guests under 18 must be accompanied by an adult. Genre: Rock

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Live Music with Pat Anderson at Keswick Vineyards
Music

Live Music with Pat Anderson

Sun, Oct 25, 2026
12:00 PM – 4:00 PM

Join us for a fantastic afternoon of live music with Pat Anderson! Pat, an Oklahoma-born and Virginia-raised roots rock singer/songwriter, is bringing his high-energy performance to the Keswick stage! Come relax with friends, sip on a bottle of wine, and enjoy the soulful tunes in a cozy setting. You won’t want to miss it!

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Session Sunday at Stinson Vineyards
Music

Session Sunday

Sun, Oct 25, 2026
1:00 PM – 4:00 PM

Session Sundays run every Sunday through October at Stinson Vineyards: relax on the patio with live music from 1-4 PM. Check Stinson's social media for performer and weather updates.

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Greg Ward at Glass House
Music

Greg Ward

Sun, Oct 25, 2026
2:00 PM – 5:00 PM

A stellar Sunday FunDay with Greg Ward returning to the tropical oasis, sharing positive vibes and groovy reggae sounds live. Sunday, October 25th, 2 to 5pm. Open to all. No cover. More about Greg Ward: https://gregwardmusic.com/ Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

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Music in the Mountains by Gina Sobel at Ducard
Music

Music in the Mountains by Gina Sobel

Sun, Oct 25, 2026
2:00 PM – 5:00 PM

Grab a glass of your favorite DuCard wine and settle in for an afternoon of entertainment with Gina Sobel. Gina is a natural improviser and accomplished on multiple instruments (flute, sax, voice). In her own music, Gina brings together elements of funk, jazz and American folk music into a fresh and compelling sound. Reservations are recommended but not required. Make yours here today.

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