56 events · This Weekend · Fri, Oct 30 – Sun, Nov 1
Friday Night Out with Kirsten Haze at Ducard
Music

Friday Night Out with Kirsten Haze

Fri, Oct 30, 2026
5:00 PM – 8:00 PM

Come on over to the winery and enjoy 1/2 price wine flights (after 4pm) and the music of Kirsten Haze. Kirsten plays a variety of folk, alt-country, roots-rock, country-blues, and a hint of jazz and swing. Order a snack from our noshing menu or bring your own. We’ve got the wine if you’ve got the time, so make sure to be here to enjoy it with us! 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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Virginia Oyster & Wine Celebration with Live Music: Lenny Burridge at Eastwood Farm and Winery
Food

Virginia Oyster & Wine Celebration with Live Music: Lenny Burridge

Fri, Oct 30, 2026
5:00 PM – 8:00 PM

Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season. Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood. Live music by Lenny Burridge, 5-8PM.

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A Haunted Supper at Hall's Tavern at Southwest Mountains Vineyards
Dinner

A Haunted Supper at Hall's Tavern

Fri, Oct 30, 2026
6:00 PM – 10:00 PM

Alfresco four-course wine dinner, haunted house tours, and a medium reading over nightcap cocktails - don't miss the fun! Held at Hall's Tavern at East End Farm, 245 Nolting Rd, Louisa, VA. Ticketed event: https://www.exploretock.com/southwestmountainsvineyards/event/622540/a-haunted-supper-at-halls-tavern

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Dara James and the Soul Disciples at Glass House
Music

Dara James and the Soul Disciples

Fri, Oct 30, 2026
6:00 PM – 8:30 PM

Dara James and the Soul Disciples return to Free Union with Blues, R&B, and a whole lot of SOUL! Featuring Dara James on guitar and vocals, Eric Franzen on organ, and Jeff Louderback on drums. Friday, October 30th, 6 to 8:30pm. Open to all. No cover. 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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Bent Theater Comedy Night at Fallen Tree Vineyard
Comedy/Improv

Bent Theater Comedy Night

Fri, Oct 30, 2026
6:30 PM – 8:30 PM

Get ready to laugh with Bent Theatre, Charlottesville’s live improv comedy troupe! Every scene is created on the spot using suggestions from the audience, so no two shows are ever the same. Grab a glass of wine, settle in, and enjoy a completely unpredictable night of comedy.

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Big City Band @ Pro Re Nata at Pro Re Nata Brewpub
Music

Big City Band @ Pro Re Nata

Fri, Oct 30, 2026
7:00 PM – 10:00 PM

Free show. Big City Band is a 6-piece rockin' country band formed in 2017, known for gritty lead vocals and family harmonies inspired by traditional country and southern rock, mixing covers and original songs.

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Grave Rave at Basic City Beer Co.
Music

Grave Rave

Fri, Oct 30, 2026
8:00 PM – 11:30 PM

THE GOLDEN AGE OF BASS MUSIC HAS RISEN FROM THE DEAD. October 30th, MOLDVTE and Faux Shaux are bringing back the sound of an era when festival trap and dubstep ruled the speakers. Welcome to GRAVE RAVE — a night of filthy bass, massive drops, throwback anthems, Halloween costumes, and the kind of energy that made the early-to-mid 2010s unforgettable. *Costumes Encouraged - But Not Required Tickets: $24 per person 8:30 PM Doors 9 - 10 PM: Faux Shaux 10 - 12: MOLDVTE Genre: Electronic Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

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Kubota Tour - Fall Color Around The Nursery at The Market at Grelen
Tour

Kubota Tour - Fall Color Around The Nursery

Sat, Oct 31, 2026
During tasting room hours

Fall Colors at Grelen Kubota Tour with Plant Manager Darren Marsh: a behind-the-scenes Holding Yard tour plus a 45-minute Kubota ride across the 1,000-acre nursery. Limited to three guests (16+). SOLD OUT. (No time listed on Grelen's website.)

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Halloween at Eastwood 🎃 at Eastwood Farm and Winery
Seasonal

Halloween at Eastwood 🎃

Sat, Oct 31, 2026
12:00 PM – 4:00 PM

Celebrate Halloween at Eastwood with a fun afternoon for the whole family! Join us on Saturday, October 31 from 12–4 PM for live music, Halloween treats, kids’ activities, and plenty of festive fun. Kids are invited to come dressed in their favorite costumes for our costume parade and prizes, while parents can enjoy a glass of wine, cider, or beer and a bite to eat.

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Live Music – Rixeyville Revival at Keswick Vineyards
Music

Live Music – Rixeyville Revival

Sat, Oct 31, 2026
12:00 PM – 4:00 PM

Come out and rock with the Rixeyville Revival Band — bringing the best hits from the ’70s through today! From classic rock to modern chart-toppers, we’ve got the groove to get you moving. Don’t miss a night of unforgettable music and high-energy fun!

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Halloween and Music in the Mountains with The Wavelength at Ducard
Music

Halloween and Music in the Mountains with The Wavelength

Sat, Oct 31, 2026
2:00 PM – 5:00 PM

Join us at DuCard this Halloween to enjoy the sounds of local band, The Wavelength. The Wavelength is a consortium of Charlottesville’s finest musicians. Led by vocalist/harmonica Waverly Milor, Larry Bisgaier on guitar/vocals, and Andre LaVelle on bass bringing you vintage rock and jazzy bluesy vibrations. Don’t be surprised if special guests join in the fun on vocals, drums, and more. Our lite noshing menu is available, or bring your own picnic! No cover. Reservations are recommended.

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Raw Beets Classic Rock with Strings at Fallen Tree Vineyard
Music

Raw Beets Classic Rock with Strings

Sat, Oct 31, 2026
2:30 PM – 5:30 PM

Raw Beets puts a fresh spin on classic rock by reworking familiar favorites through a string-driven sound. Featuring banjos, guitars, and plenty of personality, their set feels both nostalgic and totally unexpected. It’s classic rock you know—just flipped on its head

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Eastwood After Dark: Halloween Edition 👻 at Eastwood Farm and Winery
Seasonal

Eastwood After Dark: Halloween Edition 👻

Sat, Oct 31, 2026
4:00 PM – 8:00 PM

Halloween is taking over Eastwood! Put on your best costume and join us for an evening of swing dancing, live music, wine, and Halloween fun. Swing Cville will kick things off with a swing dance lesson at 4 PM, followed by live music from Zuzu’s Hot 5 from 5–8 PM. Costumes are highly encouraged! Show off your Halloween spirit in our costume contest, with prizes for the best looks.

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Halloween Party with music by Doctor Rhythm featuring King Gypsy and Jones Catering at Glass House
Music

Halloween Party with music by Doctor Rhythm featuring King Gypsy and Jones Catering

Sat, Oct 31, 2026
5:00 PM – 8:00 PM

Halloween fun – put on your costumes (if you so choose) and groove to the funky beats of Doctor Rhythm featuring King Gypsy. R&B, Blues, Soul, and Reggae tunes in the spooky tropical oasis. Saturday, October 31st, 5 to 8pm. No cover. Open to all. Jones Catering will be onsite with burgers, dogs, wings, fries and more, service beginning by 5:00pm. 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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Wide Margin at Bald Top Brewing Co.
Music

Wide Margin

Sat, Oct 31, 2026
6:00 PM – 9:00 PM

Halloween live music 6-9 PM. Wide Margin will be your guide through this All Hallows Eve, with classic rock, Americana, pop, blues and beyond, along with your favorite cold brews.

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Basicween with The Wahookies, SoulCry & XOAP at Basic City Beer Co.
Music

Basicween with The Wahookies, SoulCry & XOAP

Sat, Oct 31, 2026
8:00 PM – 11:00 PM

BASICWEEN: A HALLOWEEN NIGHT AT THE FOUNDRY Something wicked is brewing in Basic City. This Halloween, the lights go down, the volume goes up, and The Foundry opens its doors for BASICWEEN — a full night of live music, costumes, cold beer and whatever else crawls out after dark. On Saturday, October 31st, three bands descend on The Foundry stage: The WaHookies, SOULCRY and XOAP. BASICWEEN COSTUME CONTEST: stick around after SOULCRY's set for the official costume contest, with winners in three categories (Scariest, Most Seductive, Funniest). Each winner takes home a Basic City Beer Co. gift card. Doors: 6:30 PM Show: 8 PM – Late All Ages | Guests under 18 must be accompanied by an adult Genre: Rock

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Silent Book Club at Albemarle Ciderworks
Book Club

Silent Book Club

Sun, Nov 1, 2026
12:30 PM – 3:00 PM

Sip cider and read in quiet camaraderie. No assigned reading, no obligations. Bring your own book of choice. A free social event hosted in the Orchard Room, now the first Sunday of each month.

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Music in the Mountains with John Kelly at Ducard
Music

Music in the Mountains with John Kelly

Sun, Nov 1, 2026
2:00 PM – 5:00 PM

Wrap up the weekend at DuCard Vineyards with some contemporary rock and classic tunes by local singer/songwriter John Kelly. You don’t want to miss this talented artist! Grab a bottle of your favorite DuCard wine, enjoy the beautiful mountain scenery, and relax! What could be better than that? A lite noshing menu is available or bring your own snacks. No cover. Reservations are recommended.

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Paint & Sip with Blue Ridge Brushes at Hazy Mountain
Art

Paint & Sip with Blue Ridge Brushes

Sun, Nov 1, 2026
2:00 PM – 3:00 PM

Come paint with Blue Ridge Brushes at Hazy Mountain Vineyards! Design: "Autumn Morning". Instructor: Catelyn. Your ticket includes all painting materials and an 11x14 canvas. Step-by-step instruction from a professional artist, no experience necessary. Ticketed event.

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Balloon Glow at King Family Vineyards
Family

Balloon Glow

Sun, Nov 1, 2026
6:00 PM – 8:30 PM

Sunday, November 1st | Beginning at 6 PM $25 per vehicle (tickets required) Join us for a spectacular evening as four hot air balloons from Monticello Ballooning take to the sky above our polo field. Enjoy the glow from the field with food trucks, King Family wines, and an unforgettable evening under the night sky. Tickets are $25 per vehicle, so gather your friends and family, bring a lawn chair or blanket, and settle in for an evening of food, wine, and the magic of Balloon Glow at King Family Vineyards.

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